It seems like most of the weirdos I end up going out with are from Match.com. I guess I shouldn’t be surprised by that. My mom *did* say that “meeting people on the internet is weird.”

When you do match.com the typical protocol is to exchange a couple emails, talk on the phone once, and then schedule a date. It’s seriously hard to tell if you’re into someone over email and on the phone (and I hate talking on the phone, too), but that’s just the way it goes. Sometimes I get the feeling that they’re sitting in their underwear, touching themselves as we speak on the phone. Is that weird?

So anyway, one guy, who we will call Loser, emailed me a couple times. I gave him my cell and he called me. He sounded normal. He was an attorney that lived in Battery Park, and he seemed well spoken and what not. He asks me if I want to meet up on Friday night. Now, I didn’t really want to meet up with some random dude on a Friday, and potentially waste one of my weekend nights, but I didn’t have any other days free so I agreed. We decided to meet at 9 p.m. at some bar in the West Village.

Friday rolls around, and my friend S. tells me he’s down the street at this local spot we like, so I decide to meet up with him before my date. At around 8:30, Loser texts me and asks if we can meet at 9:30 instead of 9. I say sure. I go and meet up with S. and his friends, and at 9:20, just as I was about to head over for my date, Loser texts me that he can’t make it because of work. I did not text him back because there was nothing to say. The guy was obviously an ass. What kind of person makes a date with a girl, on a Friday night no less, and basically stands her up 10 minutes before the date??? I mean, for all he knows, I didn’t have any other plans that night, was in my apartment getting primped up for the date, or was already at the bar! I wasn’t any of those things, and just stayed out w/my friend S. and ended up going to an AWESOME big band concert….but Loser didn’t know that! What a jerk.

Fast forward to the summertime (I think that must have happened around February or March). My friends and I did a Hamptons share house and it was one of our weekends to go. We get out there, and decide we want to do a bottle at the club we were going. For some reason, splitting a bottle with people was almost cheaper than just ordering drinks from the bar. So we needed 2 more people to get the bottle with us. This one guy we were talking to said that he’d be interested in doing it, and probably his friend as well. We meet his friend and he looks really familiar for some reason. I couldn’t place him, but I knew I’d seen him before. Then on the way to the club, I hear someone asking him questions and turns out he’s an attorney who lives in Battery Park. Bingo. That’s Loser! He didn’t recognize me.

When we get to the club, Loser starts hitting on me big time. He was telling me how hot I was, wanted to dance with me….all up in my grill piece. I was giggling to myself at the situation, and trying to figure out what I should do, since this was clearly an opportunity for some entertainment and perhaps some payback to someone who needs a good spanking.

Eventually, as Loser was trying to dance with me (ew) I said, very sweetly, “Loser, I have a secret to tell you. But I can’t tell you now. Come find me in exactly an hour and a half and I will tell you my secret.” Loser gets all excited and in exactly an hour and a half, he comes up to me like a little puppy dog and asks me what my secret is. I think he thought I was going to say something like, “I have a big crush on you, Loser,” or, “I want to make out with you, Loser.” Instead, I gaze into his eager eyes, and say, “Loser, remember when you did match.com a few months ago? And you were supposed to meet a girl on a Friday night in the West Village but canceled on her not even 10 minutes before you were supposed to meet? That was me.” His face dropped and he said in slow motion, “oh my God. I’m going to regret that.” And then he tried to excuse himself by saying, “oh, you know how match.com is….so weird meeting people from there….” And I basically told him he needed to grow a set because that was just rude and inconsiderate no matter how you slice it.

So Loser realizes that I’m for sure not gonna be hooking up with him that night, and proceeds to hit on everything that moves. He literally hit on every girl in there. My friend R.A. comes up to him around oh, 1:30 a.m. and goes, “you’re a ho” in a cute, sort of jokingly way. Kind of like you’d say it to your girlfriend or something when she’s shaking it for some dude, but you all thought it was funny.

At 4:00 a.m., the club was closing down and it was time for everyone to pay their part of the bottle. One of my friends had put it on her credit card so everyone had to give her cash. R.A. was standing by the table, probably getting her money out, when Loser comes up to her and puts his face in her face and yells at her, “you’re a f*%$’ing BITCH!” R.A. is totally shocked, has no idea where that came from, and they start arguing.

Somehow I managed to get Loser to pay his portion of the bottle to my friend. His friend, on the other hand, told us that he didn’t have the money on him and would pay her the next day.

We go back to the sharehouse and R.A. goes outside on the steps of the house. Loser goes out there to where she is. R.A. is about 5’4 and Loser is about 6’3. Loser goes up to R.A., basically bows up at her and gets in her face like he wants to fight, and starts yelling at her what a “bitch” she is. R.A. holds her ground and is thinking, is this guy actually trying to fight me or something? Finally she just goes back inside. Until this point in my life, I had never heard of a guy trying to start a fight with a girl. Well, except for insane, violent men who beat their wives. Like Ike Turner.

The next day, we are all lying by the pool. I go inside to the kitchen to get some water. Loser and two of his friends are in there. Loser tries to be nice to me and I just get my water, not wanting any more drama. Then one of his friends says something about the previous night. I say, in a nice way, as to not start any sort of drama again, “you know, Loser, that wasn’t cool yelling at R.A. like that last night. I know we were all drunk but….” Thinking that he would say something along the lines of, “I’m really sorry, I was really drunk and stupid” but no, he starts yelling at me and Loser personality #2 comes back to life. I open the door to the pool and yell, “hey guys, is it ok if I throw this asshole in the pool?” or something like that. I just left him in the kitchen screaming at me.

We all know that losers hang out with other losers, and his friend, who owed my friend a bunch of money, tried to tell her he’d send her a check for it since the ATM charged him $1.95 every time he took money out. We all said heeeell no getcher-ass in there and give us our money, bitch. He did.

Dear Loser,

Here is my advice: go to the Yellow Pages, look under “Psychologists” and then look under “Psychologist for insane narcissistic crazy people” and call a few of those guys. Schedule appointments for the next 5 years, twice a week, 1-hour sessions. You may even want to just commit yourself. Perhaps it’s better that you aren’t running loose. The compassionate side of me really hopes that you get help and the raging bitch side of me says that if I ever see you out with a girl, I will go up to you and provoke you so that she can see what a lunatic you are.

Hugs and Kisses,

A.D.

I went to brunch with a guy friend of mine, we’ll just call him J, and he told me how he had been doing some online dating recently. A couple of months ago, he met up with a woman for dinner (first date. Actually, come to think of it, I need to advise him to not take girls out to dinner on a first date…that gets expensive! But he’s classy like that. Anyway….) So they had a nice dinner, and she revealed that she wanted to write a book on dating tips for both men and women.
After their date, he emailed her saying it was nice meeting her blah blah blah. She writes him back that although she thought he was a fantastic person, she didn’t feel any “chemistry.” Actually, her email to him was REALLY GOOD! She complimented him on his terrific manners (he’s British, which maybe has something to do with the fact that he acts like a total gentleman all the time…wait, I’ve met several crass Brits, so maybe it’s his upbringing….) and commented that that is a rare quality in men in NYC (I AGREE, GIRLFRIEND!). And she was honest, but in a super nice way, which I give her a lot of credit for (although I thought her email was very scripted, but whatever. I still thought she was very cool with that one).
So he emails her back being like, that’s cool, thanks for being honest, maybe you should give me some tips “haha.” And she obviously gets all excited and was MORE than happy to share her “expertise”. I thought about 70% of her observations were pretty accurate, except she kiiiiind of wants every guy to be the guy SHE wants to date. I think that everyone should be who they are not “plan” things to say, because then it just comes out all weird. I also think that people should keep their own personal style, because that expresses who you are. Anyway, I thought her observations/tips were interesting so I wanted to post it on our blog :) here is what she emailed him…. (I bolded and italicized my thoughts on what she said)

“Okay.  For starters, you have to learn to chill out a little. Move a bit slower.  I know you were nervous.  Its cool. I think it’s cute if a guy is a little nervous!  It happens to the best of us.  But you find ways to relax before you go on a date.  Don’t drink coffee!!!  lol.  If you are nervous that will only make it worse.  If anything, have a glass of wine before you go out. You’re telling people to drink before they meet up with someone??? Um ok…  Wine will melo you out.  You want to come across as cool, relaxed, laid back, and confident.  Confidence is key!!! Amen, sister.  Don’t keep it in your head that she is going to reject you because you set yourself for failure when you do this.  Begin saying out loud to yourself everyday that you are desirable.  Say positive affirmations that will change whatever mental blocks you have.  Don’t try to convince a woman that you are right for her or that you are a good man by telling her so.  That’s too aggressive and comes across as desperate. OK I see your point, but stop trying to be all Tony Robbins on him.
  You are a good catch. You were a professional squash player and now you have a business as a coach.  That’s awesome.  It says a lot about you.  Also,  I know you mentioned the culture difference, but women love men from London.  You have to use that to your advantage. Huh?
  You present good manners and proper etiquette (p.s. I just had to fix her spelling - she spelled “etiquette” as “edicate”. Learn to spell, lady! Sorry, pet peeve of mine. This is good.  One less thing for you to learn.  Being a gentleman is verrrrrrry important.  You just have to learn to be a bit more suave. Agreed on the good manners/gentleman part. Why is that such a rare quality these days??
  You are a very good looking man but it doesn’t matter because you hide it.  If you want to impress her, you want to dress the occasion.  Dress to impress.  You are a man with style and class and when you take a lady out you want to look nice for her.  You don’t have to wear a tux or a suit. But whatever you wear should be stylish and should say I’m cool, I’m laid back, I am dignified, I am a person of value, you want to be with me.  lol.  Sounds corny but its true.  If you want i’ll help you shop.  Also, you may want to grow out some of those curls and throw a little gel in it.  women like hair.  You have all your hair.  If you let it grow out some it will give you a more youthful appearance. Most of this paragraph is just ridiculous. My friend wasn’t dressed pooly, but he has his own personal style and I think he should stick with that!! You can take him shopping as long as you don’t dress him up as something he’s not….. Although I do agree men should dress nicely when going on a date. I hate that untucked shirt and jeans look. It looks sloppy to me.
  Lastly, always remember that flattery will get you EVERYWHERE!!!  Just make sure that when you are offering a complement it has to have some relevance.  Its okay to embellish a little, just don’t say anything completely off the wall and make sure you say it without blinking.  Understand?  Women love this stuff.  OK, Dale Carnegie gives much better advice about this stuff - you should complement people but you need to GENUINELY MEAN IT. And it’s easy to find something you genuinely like about someone. I think maybe this is what she meant, but it’s a little deeper than that….you need to take a genuine interest in the other person, and you’ll genuinely find something that you like about them. In fact, if you’d advise these boys to concentrate on taking a genuine interest in their date, they probably would forget they are nervous to begin with…
  Now, everything has to be applied with tact.  When you approach a woman you want to come across as suave.  You are confident.  Look her straight in the eyes when you greet her.  Smile and let your eyes smile too, to let her know you like what you see.  This eye contact is how you create a connection.  Tell her how beautiful she looks.  Be creative.  Say something like what you said to me, only romance it a bit, “You are far more beautiful than your photo.” Again, if some guy said this to me and it wasn’t organic, I’d be able to tell. GENUINE…is key. when you reach for her hand, kiss it or shake it slowly while maintaining eye contact. This has the potential to be creepy….  Keep the compliments flowing over the course of the evening. Don’t over do it.  Remember.  Be cool.  Be careful what you talk about on the first date.  You want it to be positive always.  Don’t talk about thigs you hate.  I agree! I like positivity. Negative thoughts and feelings are a no no! Talk about things you love. Don’t talk about crazy past loves. Tooooottally agree!!  Talk about good things so it will create good feeling.    I think that’s pretty much it.  lol.  If you need anymore advice let me know.   
-R. a.k.a. casanova coach   ;)
So that was this woman’s email to him. Clearly, she has some good points in there, but I really think the bottom line is to be yourself. And let’s be honest, all those “suave” “laid back” men that you meet that don’t seem nervous at all, probably aren’t because they go through women like they’re socks. And you don’t want those men.
Dear Ms. Casanova Coach,
I’m catchin what you’re throwin, pickin up what you’re putting down, but please don’t try and make men into the man that YOU think they should be. Not all those “suave” men are that great, and just because someone dresses like they just walked out of their MBA program at Yale doesn’t mean that they are worth getting to know. However, I dig your style, and I hope you’ll work on improving your spelling because there were a lot of serious errors that I had to fix in that email. 
Thanks for caring,
A.D.
 

Dating in New York can be exhausting for women. Men don’t call, or they call too much. They forget to mention they have a girlfriend, or 12 kids, or that they sell drugs to children…..For some reason, my friend R.A. and I don’t feel like this is necessarily a bad thing….we find it INCREDIBLY entertaining. I mean, you just can’t make this stuff up.  One of my friends was unable to meet up with a guy SHE HAD NEVER MET BEFORE one night (from JDate), and so he texted her, “I hope you choke and die.” Now, all you can really do in that situation is laugh. Or call the police I guess. And be glad you never met up with him. But truly, some of the funniest stories my friends and I have involve some of the really strange men that we’ve dated. We realized that we just HAVE to write this down! I’m sorry, I know us girls can be a little wacko in the sacko sometimes, but guys in this city take the whole upside down cake when it comes to crazy.

And honestly, no matter how many times we’re disappointed, heart broken, or dejected. I really believe in finding humor in every situation. I promise that there is.

 My friend and I recently found ourselves having both broken up with our boyfriends. I dated this guy for 9 months which went something like this…fun fun fun..this will be a great summer fling…oh wait I like him…wait I love him!….oh wait he’s actually got some SERIOUS character flaws….oh wow this guy is really not a good person….goodbye! That pretty much sums that up. My friend’s story was quite different, but we both had to break up with these guys, for different reasons, but break up none-the-less.

So, I find my friend and I in a position of being VERY happy to be single. It’s like a HUGE burden has been lifted. We’re happy to be working on making our own lives the fullest they can be, we’re both into challenging ourselves physically and mentally, and just basically don’t feel like putting up with any bullshit that isn’t our own (is that so bad??). But alas, that attitude just seems to bring out all the men in NYC. And let’s be honest, we’re still girls who like to have fun, so we don’t want to be TOTALLY single all the time (duh!)

That brings us to present. My last relationship left me wanting to just sit here and sing the MJB song “no more drama in my life”. I can’t even take the drama on American Idol at this point. That being said, I’m still the same ol’ me and I like boys. So, there was a week I was in purgatory break up land with my boyfriend (I broke up with him, he didn’t get it, so I had to do it again), and I met two guys (that ALWAYS HAPPENS. I swear, these boys just SMELL the break up on you or something!). The first somehow found me on facebook (I know, seems creepy, but whatever. His introductory email, entitled, “How’s this for creepy…”  made me laugh so I had to give him a chance!). Then I ran into a guy I had met a couple years ago in the Hamptons. So, I had tried to break up with my boyfriend a few days before this, but he didn’t seem to get that I was serious about it. So I guess technically I wasn’t single just yet (however, I got it through his head as soon as I could, which happened to be the day before Valentines day. Eek.) Anyway, the second boy, let’s call him Purple, actually tried to make out with me at the bar where I ran into him.  Ew! Why do guys – who are not on “Jersey Shore” – try to do that?? And why do they get all offended when we refuse to make out with them?? You nasty!

The day after Purple tried to make out with me in a dirty bar (I just vomited in my mouth) I broke up with my boyfriend and it actually was pretty heartbreaking even though it REALLY needed to happen. We both cried, and I was really sad. Well, really sad until I left his building, and then I wasn’t sad after that, except that I still miss his dog sometimes. He was a bulldog and I called him Mr. Puppyface. Aw man, I just got sad.

Ok - I’m over it. Bye Mr. Puppyface I’ll miss you and your little wrinkles I liked to smoosh :(

Facebook dude actually asks me to meet up with him that very night. I thought, ok sure…what better way to move on than by going out with someone else before the proverbial body’s even cold?? So I meet up with him and he was well dressed, attractive, seemingly normal…. but I got there and then just did NOT feel like being on a date. I just wanted to hang out with my friends or watch Glee, but NOT this. Not that he was being inappropriate or anything, but I was just not feeling like delving into the depths of my life with anyone new just yet. That’s like, 3^rd 4^th 5^th date stuff anyway.  I think.  I left that date feeling like I should go out with him one more time, since I was so drained from earlier that day.  He asks me out for Thursday, and I tell him that I am supposed to meet some friends at a bar that night and would he like to come. He said sure! Thursday rolls around, he’s still coming. Then I said I’d be there at 9:00 and probably wouldn’t stay past 11 or 12 because I needed to get up early. Well, this is NOT something you tell a guy, because they always want to think that there is a chance you’ll have sex with them that night. I already knew this, but I just didn’t care, and in some ways I just wanted him to leave me alone for now. He makes some excuse about having to do something with work. He later, at about 10:30, texts me and calls me that he’s really drunk and wants to see me. No, I’m not interpreting. He literally texted me “I’m drunk and want to see you”.  I’m sorry, did your brain just fall out of your head?  Or did your penis just learn how to use a blackberry?

Needless to say, I did not respond to this nonsense, and he texted me and called me the next day apologizing. Unfortunately, facebook boy, you’ve already made a REALLY bad impression on me.  And really?? The blatantly disrespectful drunk text combined with him flaking out on me last minute, combined with the fact that I knew him less than the girl at the Starbucks counter just made me completely lose interest.

Truth is, if this had happened at a later time, I would have just let it go. We all make bad decisions at one point or another. But c’mon.  That was just REALLY unattractive. And I’ll be honest, there were a couple of things he said on our first “date” like, asking me how many kids I wanted to have, telling me he’d love to meet my family one day….  that I was a liiiiiittle bit weirded out by. But obviously, one can judge by the previous “I love you. What’s your name again?” post (SEE BELOW) that I tend to ignore the crazy things people say in hopes that they aren’t, actually, crazy.

Facebook guy actually kept trying to get me to go out with him (“I’m having champagne at the Ritz with some clients, would love if you’d join…” and instead of being honest about why I thought he was a douche bag, I just told him that I wasn’t ready to date yet (which, let’s be honest, is true). And he kept trying to figure out why I wasn’t in to him…was I getting back with my ex, did I not find him attractive… and for some reason it never occurred to him that the whole blowing me off then drunk dialing me experience totally turned me off.  Whenever you try to school some guy, it always turns into drama or you have to delve into way more than you really even care, and I just didn’t feel like it. To this day, this guy still texts me, contacts me, trying to get us to be “friends”.  I don’t wanna.

Moving forward, me still super psyched to be single, we go to the second guy - Purple -who meanwhile was trying to hang out with me. Ok, by hang out, I mean, he would text me to see if I was going to be out later…if I was out currently….no real attempts on his part to actually like, take me OUT. C’mon. Seriously? Needless to say, I keeps it real. I’m not going to make out with you in a dirty bar, buddy. His timing was just offensive. But, although it was obvious that Purple just wanted to get in my pants, let’s be honest: since I just broke up with a guy, I sort of want to get in his pants, too. But come on. Work it a little. You can put the idea in our heads but you gotta work it if you want that idea to become a reality!

So, I put zero thought into this guy because of the previous and a couple more attempts on his part to get in my pants, always at his convenience. At some point in this (I honestly don’t remember how long this went on) he invited me to go bowling with him and his friends. Yay! I love bowling! I brought a girl friend of mine and we had so much fun. We bowled, I won a game, we danced around all over the city. I made out with Purple this night (NOT at a bar) and I stayed over and didn’t sleep with him. He was surprisingly a total gentleman, very respectful, and not jerk-y at all. Decided I’d been a little too persnickety in my previous judgment and gave him the benefit of the doubt.

I can’t really remember but I think it was a couple more weeks before I finally slept with him. It’s not that I have THAT horrible of a memory, but I was legit busy and had other things on my mind. When I finally slept with him, he had actually taken me out to dinner that night and I had a great time with him, and I had gotten to know him better by this point. And let’s be honest, I needed to get my rebound on! (Why do we feel like we need to solidify a break up by sleeping with someone else? That’s dumb. Hmm). After that, Purple and I still hung out, but I didn’t think he was bringing it enough to keep my fine ass comin’ round. 80% of the time he would ask me to hang out the day of and last minute which a) doesn’t always work with my crazy life these days and b) is sort of rude and insulting. Not that I should’ve been surprised by any of this….

After this went on a few weeks, with mainly half-ass attempts on his part to see me, I just started to lose interest. Then I hung out with him one night, and it occurred to me that I DID kind of like him more than I thought! (but this always happens…and why wouldn’t I want it to??) When we DID hang out together, I had a really good time! But that thought immediately made me irritated and offended that he thought he could put hardly any effort in and I’d still stick around.  I mean, this was obvious from the beginning but…still! I’m also a firm believer that if some guy is really into you, you don’t have to complain about any lame attempts on his part to hang out. So I decided I was done with this nonsense because, as previously stated, I keeps it real!  I also just didn’t feel like feeling irritated, plain and simple.

So, being the mature person I am, and occasionally *not* keeping it real, the way I ended things was inviting him to a party, getting mad at him for a stupid reason, and texting him that he is “slightly retarded” and that I was offended by his “ lack of depth and propriety”.  Apparently I went and took crazy pills that day. It might be one of the meanest (and stupidest) things I’ve said to someone, but I apparently had NO filter going on at the moment. I sent that, reread it, and cried from laughing so hard at myself. Who the hell says “propriety” anymore except for Mr. Darcy?? (Aside - Pride and Prejudice…best book EVER). Haha. Felt bad about that later, because he really didn’t deserve THAT.  However, these boys know how to behave appropriately, they just choose not to.  And they play dumb when you call them out but you know, ignorance should not be rewarded. Purple got all defensive, “I ask you out all the time!” but I was already irritated…end of story.

But honestly, not to go off on a tangent here, but what are we supposed to do when we don’t want to see a guy anymore? Mysteriously ignore their phone calls? (No, mean…) Tell them I “don’t want to see you anymore”? (leads to the previous brutal honesty). Well, I guess I could have given some “I don’t want to date anyone right now” number  (which could lead to behavior like facebook guy’s) but  I think I like the “truth hurts” thing better, and wish I would have told facebook guy what his problem was. Actually, I think if some guy, who wasn’t in to me was like, “ya know, you’re cool, but your breath smells ALL the time” or something, I would be a little shocked, but I would never forget to check my breath before leaving my house again. Ya know? I like constructive criticism. I mean, as long as its constructive. I can’t help that my feet are big or anything. Ha.

Or just honesty. I have a guy friend who sleeps with girls all the time, date her for a little while, then break up with her. And they sit there and wonder what they did wrong, or why he doesn’t like them, and the truth is, HE JUST WANTS SOME NEW PUTANG. It’s really that simple. They could be Jenna Jameson and he’d STILL get tired of her after a few weeks. So, I wish I could go up to those girls and tell them that “it’s not you it REALLY IS HIM.” (Sorry darlin, for when you read this. But I’ve already said this all to your face J love you).

Anyway, back to my story…with all the drama I’m trying to avoid I should have been happy to find a guy who is so one dimensional and had zero interest in actually dating me!  But I know myself, and I know that I can’t have unemotional relationships with people for too long. And I don’t want that to change either.

MEANWHILE, in these past 2 months that I’ve broken up from my boyfriend, I get random texts from him basically saying he misses having sex with me. Well, all I can say is THAT was never a problem by any means.  That’s the other thing…..making love to someone that you know and care about is just WAY better than any other kind (to me, anyway). Speaking of, he just texted me AGAIN while I write this. He said that he thinks about all the good times we’ve had and how he thinks “something is in the air.” No, sweetie, something’s in YOUR air, mine’s all clear. Thanks.

Dear Facebook guy and Purple:

                Guys, you can’t be all up in someone’s Koolaid if you don’t even know the flava! I don’t know where you two ever got the idea that you were so fabulous that you didn’t have to put any effort in to impressing a woman. And I KNOW I didn’t give either of you the impression that I’m easily impressed! Good luck with all your drunk dialing. I am sure there is someone out there unbalanced enough to just eat that up.

Always keepin’ it real,

A.D.

A few months after I graduated college, I moved into my parents’ cramped one bedroom apartment on the Upper East side of Manhattan. Most kids I knew had the luxury of doing the Murray Hill-‘my parents are paying for my rent’-doorman situation, or were moving home to their nice suburban enclaves while commuting into Manhattan. I was sleeping on an air mattress on the floor of their apartment. Did I mention when they had a vermin problem, I had to sleep on the dining room table? As a semi-spoiled JAP, who was currently working four part time jobs within the entertainment industry and media industries to get my “foot in the door”, post-college, I was not a happy puppy and decided my parents were to blame, for not rewarding my diligence. I didn’t say I wasn’t a brat.

I would come home very late from work, and I became very chatty with the overnight doorman. He was a tall delicious drink of water, he was Puerto Rican, but looked like a Greek/Puerto Rican Mix. At first, it was just playful banter, consisting of nothing substantial. We both loved music. He was interested in all the jobs I was working, as well. He became a good listener, and he worked week nights in a building where mainly older residents resided and never ventured downstairs past 11 p.m.

Ironically, a relationship of a sexual nature did not take place until after I moved out of my parents apartment. We had flirted, kissed, groped each other in the closet where they store tenant’s dry cleaning and laundry, but it never went any further. 6 months later I landed a full time job and an apartment that was only 5 blocks away from my parents’ building. He started asking me out on dates immediately and coming over to my apartment. I decided to return the favor, and I still continued to visit him on his overnight shifts, hiding in closets, the doorman’s break room, shutting off the cameras in the elevators, the mail room. Pretty run of the mill stuff. 

Anywhere in this little residential building you could think of, we did it in. There were two times where the doorman had to hide me in the “dry cleaning” closet, as he opened the door for my dad as he walked our dog at 5 a.m. I tried so hard to keep it together and not laugh or utter a peep.

I finally told my parents I was seeing the doorman, I never told them I was desecrating their building after hours. It did not phase them for one minute, that (A) He was there was their doorman. (B) He was Puerto Rican (C) He did not have a college education. (D) He had a daughter. They were beyond accepting of him, they allowed him to come to passover Seders and Jewish holidays. He was also always at my apartment fixing things and staying over and I basically moved into his apartment in Brooklyn and starting looking in on his mother who was a lonely widower. How did this turn into a real relationship? This was supposed to be pissing my parents off?

We were together for a little under 3 years, yes 3 years, then afterward he was my glorified Fuck buddy for a while, whenever I had a little bit of downtime in between relationships, he would be dial-a-Fuck. I wore just his doorman jacket as my Halloween costume with thigh high boots and a smile one year. People saw me walking around with the management company’s name on the jacket and were like “I write my rent checks out to them” Shock and Awe people, that is what I go for.

One day in 2006, this all came to a screeching halt, I get a call from a 917 number I do not know, the doorman had texted me a few days before and called asking and telling me not to pick up from any random numbers. I was suspicious, especially as more random calls, kept filtering in. So as a creature of curiosity, I pick up, it’s his baby mama, who I knew of, I had never met, (never wanted to FYI) but knew of. She basically told me, the doorman has been leading a crazy double life. She had recently stolen his SIM card in cell phone and copied down every number in his phone and just started dialing, pouncing like a lion for information. See, the doorman had gotten her into $50,000 worth of debt. That fancy BMW he drove around from her dealership she worked at, was in her name and he was terrible at making payments. He also had 2 residences, one which he shared with her and his daughter in Sheepshead Bay and the other one, which I had seen where his mother lived in the same building, in Midwood. He was a serial cheater, he was with her while he and I were together, and many other “bitches and ho’s” and she said. She said he slept anything with a tight ass or p**sy. I was literally shaking, I mean I was no longer in love with the man, but to think all this time, I was trying to teach my parents a lesson, he was just a phase, and he has been playing me and everyone else like a violin. He was the Puerto Rican Ron Jeremy, literally and figuratively and Dirk Diggler in every sense. The baby mama, asked me to meet up with her, I almost did twice, but canceled, I just couldn’t face her, knowing I was the HO for SHO, even if I never meant to be. I got to know his daughter when we were together and now how would she know me?

I told my parents about the whole situation and they were not surprised. I swear nothing phases them! They said they knew the doorman was always a phase, I would never marry him and all the the material things in his life, that he was able afford never seemed right, but never seemed wrong enough to be truly illegal or worth starting a fight with me over or placing a stake in our relationship. I was shocked at how evolved my parents truly were. Unfortunately, I put them through so much more relationship 911 in some cupid posts to come, but they took it like champs!

Being newly single after years of being a monogamy whore, I am allowing friends and colleagues to set me up. I was super intrigued when my co-workers wanted to set me up with one of my favorite television actors’ producing partners.  Now, I was skeptical of the set up as I have started at this job rather recently and I was wondering how these people viewed me.  I am jokingly viewed as a sardonic and jovial person, who sometimes lacks a filter when inebriated, but I was wondering, since we work in marketing, how they would “pitch me”.  Well ladies and gentleman, I got a glimpse into the circus that is dysfunctional dating. Now, let me preface this by saying my new theory in dating is being less snooty and more open-minded and going out with more people - people I wouldn’t gone out with in the past. I have a penchant for writing people off when they do something small to piss me off and I am trying to be open minded, more specifically in the looks department.

So, first off, my work colleagues give this guy all my contact info, email, phone number, everything under the sun and how does he get at me first? Old School AOL instant messenger, yea, hi, 1996 called they want their dial up and contact mechanism back! They also want back their cyber sex and chat rooms. I am not even on real “AIM”, it goes to my blackberry, so I get bombarded by these messages in text message form, by a user name, that I of course, do not recognize. The user name looks pretty much like a porn user name and has the letters “XXX” in it, so I really think I am getting porn spammed for my cyber panties or something, but no I am not.  We have a brief chat and I notice this man, who has somewhat of an issue with self-deprecation, literally tells me he should stop talking a few times, so he does not “screw this up”. Clue Number One Sherlock, this date will not bode well for either one of us.

OK, Remember, I am being open minded.

So I give him my number, he asks me how many suitors, have “said” number and I replied, that is really none of his business, in a nicer manner.  I get a missed called from  a “347” area code number that night, I do not pick up, because we all know we screen unknown numbers.  I assume it is him, but no message was left, the next day a call from a 917 number, and a message in a super effeminate sounding voice in the longest verbal diarrhea message I have ever heard. 

I am slightly turned off, wait a day to call back, because he also called at 11pm, which old me would have pre-judged.  So, I call him back the next day and we have an interesting conversation for the first few minutes - he is like a kid who was never given Adderall - and we speak of stories from within the entertainment industry and about his television actor friend who he owns a production company with.  He quickly delves too quickly my relationship past, what I am looking for and then *GASP* asked me what kind of tampons I used. Yes, you heard me right, he said he was joking, he works from home and when he was on the phone he saw an old box in his bathroom cabinet and it was a bad joke. He also tells me the last two girls he went out with were deaf and bipolar. Now, I want to go running for the hills, but I remember these are my work colleagues setting me up, I adore the actor he works with in his production company and if anything, maybe it could be a good networking experience?  Maybe?

So we schedule a date at Library Bar, then he tells me he had an allergy attack the day before and needs to reschedule. I hesitantly say yes (very skeptical), I tell him a specific date I can see him the following week (double-booking him with another date, with a guy I actually like later on, so the night is not a complete waste) and we are set. Well, before then, I get a text from a different 347 number and a missed call from a 212 number, yea this kid has 4 phones, i realize like an hour before the date, he thought our date was Thurs, it was weds and i forward him text proof as he tells me I am wrong. He feels like an ass, I am ready to rip him one, so yes, he shows up, because if he did not we were never going out. Trust.

Stage Left: Please enter the hobbit with spikey Backstreet Boy at 33 years old. I am only a smidge over 5 feet myself, but he was maybe 5’4 and I was in 4-inch heels. The conversation is strained, he pays me compliments telling me I am attractive, but besides that he continues to take me down a peg. He continues to give me a hard time the whole date and he is so proud I showed up and all and could take the time out of my busy night.  He ALSO tells me my standards are too high, he continues to tell the waitress to bring me more booze, because I look like I am miserable. It was so bad, in the bathroom, where I usually quickly respond mid-date to BBMS and texts, I responded to a missed call from a friend and said I might need a help phone call to save me.

Luckily, I just had the balls to tell “the hobbit”, I was going to head home and I was tired after a long day of work. He asks me if this is the worst date he has ever been on, I said no definitely not, I just found him odd and lacking a filter and now I see where my personality could be, if I do not issue some restraint. He found that comment charming. So as I leave, I receive a text message a few minutes later, had a great time, cannot wait to hang again, from another number this time “646” area code!! REALLY, is this guy Jack Bauer from 24?  Why does he have so many numbers?? Now, I never do not respond to messages, so I said, “Not gonna happen, best of luck to you in all your dating and Tampax seeking adventures”.

THE ACTOR:

When I moved to New York, I had really never dated before. I had one college boyfriend, one post college boyfriend (who was SUUUUCH a jerk – maybe I’ll blog about that craziness later) but I mean, I never had some guy that I didn’t know be like, “hey, what’s your name? Wanna go out some time?” I always lived in small enough communities where it didn’t tend to happen like that. There wasn’t anyone you didn’t know. So anyway,  I was a blank slate to the whole formal dating scene, which is my excuse for being so naïve in the following lil story…

One day, I was walking to my new job, a few weeks after moving here, and a guy followed me into the elevator.

Guy: “hey, so, do you know which floor ____ is on?

Me: “no…I actually just started working here. Sorry”

Guy: “that’s cool. Actually, I made that up. I thought you were really pretty so I followed you in here. Do you want to go out some time?”

Me. “um…ok….”

Guy” k what’s your number?

Me: “617-…..”

Guy (as I get off elevator to my floor): “Ok awesome I’ll call you soon!”

Me. Flabergasted.

I went out with the guy, and he told me how he used to be an Investment Banker but left all that Wall Street nonsense to pursue acting full time. I thought that was great. Pursue your dreams! I love people who are passionate about something! We went out a couple of times and made out and stuff. After a few weeks, I did the dirty with him. The next time we hung out, we go to dinner or something, and he tells me he has a gift for me.  So we go back to his apartment so that he can give me the gift. The gift was this red picture album with “I Love You” written in gold letters on the front. I say the first thing that comes to my mind,“ Why does this say ‘I Love You’ ?” “oh…I didn’t even notice that….I thought it was pretty” he says,  all awkward. Was he expecting me to go, “oh my gosh, I love you too!” I didn’t get it, and I still don’t.  I just thought, he couldn’t POSSIBLY mean that – he doesn’t even know my obsession with Clint Eastwood or that I never clean out my coffee pot or a million other things I think someone should know and accept before they say they love me! But for some reason I just let that go, and did not think he was crazy at this point, because I thought, SURELY, he couldn’t be dropping the L bomb on me!  Because that would mean the guy is seriously unhinged!  Well, to most people that would probably be a big red blinking sign that says, “STOP DATING THIS GUY” but stupid me continues to date him. Here are the things that I found out after knowing him for a bit longer:

1. He gets a spray tans on a semi-regular basis, to bring out his abs in photo shoots (the guy had a pretty sick body).
2. He kept those Etteman’s cakes that you see at Duane Reade in his apartment because every now and then, he would literally binge eat on them all day long (he revealed this to me when I found a STASH of them plus tons of other sweets).
3. He was on a whole slew of prescription pills. One for going to sleep. One for waking up. One for depression. One to counteract any side effects the previous three have, and who knows what else. MAYBE I’m being insensitive, but to me he seemed like a rich New York City kid that didn’t understand why he was unhappy so he just took pills. 
4. He had a serious problem with exaggerating the truth to the point he was basically lying. I don’t like being lied to, because I usually just assume people are telling me the truth and it sucks when you eventually discover they aren’t :(

I’m actually embarrassed to say that I saw him on and off for several months (he was fun, I’m into fun…whatever!). I’m quite positive he was seeing 100 other girls, and I’m pretty sure we ran in to one of them when we were together one time. When Christmas came around, and we were not seeing each other at the time, he showed up at my work with a GARBAGE BAG full of wrapped up presents which I’m pretty sure were from Duane Reade  Actually, I think the infamous “I Love You” album was from Duane Reade. I think that while he was waiting on his 25 prescriptions, he wandered around the drug store, all depressed, bought some Etteman’s goodies, some gifts for all his women, and then got his pills and went home.  I’d like to think he was just a little melodramatic because he was an actor or something, but let’s be honest he needs some professional help.

(DISCLAIMER: I have nothing against Duane Reade. I buy tons of stuff from there. And I have nothing against receiving presents from Duane Reade. My point is that I found it odd that he literally raided a drug store to buy 25 items that do not make ANY sense to give someone.)

Dear Actor:

I hope you’ve finally found a girl who appreciates “I Love You” picture albums from Duane Reade, and not only that, but she doesn’t mind getting them before you even know her last name.

Happy Spray Tanning,

A.D.

I met Mr. Attorney on Match.com. He seemed cute. Smart. Whatever. You can’t really tell anything about these folks until you meet them in person. So I agree to meet him at 14^th and 8^th and we can find a place from there. As soon as he walks up and says hi, I have to admit that I did make a snap judgment that I had no interest in him. He was really good looking but there was just soooomething that turned me off. Anyway, we go to this hole-in-the-wall bar (hmmm…just remembered I left my credit card there the other night uh oh) and he pays for a round of drinks. Drinks are $6 there. Very cheap in NYC.  I run in to a couple of people I know, I chat with them a little, not really caring that I sort of ignored this guy for a little while. Then I feel like I’m being rude, and I sit down and take a genuine interest in what he has to say. He’s an attorney, he likes NYC, blah blah blah. I politely ask if he’d like another drink and he lets me go up there and pay for another round. Now, I’m all about splitting tabs in NYC, cause this is an expensive city, but for such a cheap place and our first date I thought that was a little weird that he didn’t offer.

Anyway, he asks me if I’m hungry and I say not really but I’d get something to eat with him if he wanted. He suggests the Mexican restaurant across the street. I say, sure. We go over there, sit down, I order a small appetizer and he orders an entrée. We talked some more and I actually started to like him a little better. Like, hmm, maybe I’ll go out with him again. Then later after he’d finished his meal the bill comes. I pull out my credit card since I didn’t have any cash, and he lets me put it in there and split the WHOLE bill with him. OK, I had a $5 appetizer and you had a $15 meal, buddy. Give me a break! I was completely turned off.  In retrospect, I think it should have called him out on that. How rude! And you call yourself a southern boy…..

So we leave the restaurant and say goodbye. I figured that he just wasn’t in to me and figured he didn’t want to spend any more money than he had too. Ok whatever.  But no. He emails me, calls me, IMs me, and texts me to hang out again. I email him some bullshit about having just gotten out of a relationship and didn’t think I was ready. He says oh ok, I’ve been in that boat, do I want to be just friends with benefits? (What???) I guess I have to give him props for asking, but …..really??? He also prefaced his email with saying how hot he thought I was. So, let’s see. If I were a dude, and I was really attracted to some girl, and I wasn’t 14 and had mental problems, wouldn’t I think to buy the girl’s $5 appetizer on the first date? I’m just sayin. I ain’t no money grubber for sho, but come ON.

Dear Mr. Attorney,

                Thank you for not paying for your food and not being a gentleman. You saved me the trouble of ever having to go out with you to find out that you’re a tool bag, and you gave me a really good laugh. I hope it’s all working out for you.

Happy “Friend” hunting,

A.D.

Jazz Musician Ray* and I met on the interwebs.  After a few witty email exchanges, he asks me to meet him for post-work drinks on a Wednesday evening.  I’m leaving to meet him near my office when 30 minutes before the date I receive a mysterious text asking me to meet him at “the Apple store.”  And so our magical date begins around Ipods and Macbooks. 

“I just dropped off my laptop to get a music program installed and I’m already jonesing to compose,” he said, wearing thick-framed glasses and a shaggy do.  His aesthetic was something between hipster and lumberjack. Looked like his profile picture.  Good start.

JMR composed and taught jazz for one of the NYC conservatories. He was an arteeestt. 

“Let’s go to the Diner,” he suggests.  Sure.  No matter that it was 10:30 p.m. by this point and I had no desire to sit through an entire first-date-potentially-awkward-convo meal.  Despite his three-course diner meal and my slow consumption of a Stella, conversation flowed (albeit centering on his work, his musical dreams, his “vision” and I couldn’t give a shit about Jazz).  Three hours later, it’s time for the date to end.  Not the best, but not the worst, I thought.  He’s cute enough to see again. 

We’re waiting for the check when JMR proclaims, “Let’s just get out of here.” 

“What do you mean?” I reply.  Wondering if this is a weird, post-date booty call or he’s actually suggesting that we skip out on the bill.  “I mean, they obviously don’t want us to pay so we should just walk out,” he states.  I search his face for a hint of sarcasm.  He cannot be fucking serious.  Oh, but he was.  After I tell him that I try to keep things “on the up and up” as a lawyer, we receive the check. 

“You can just give me 6 bucks for the Stella.”  That’s right.  After suggesting we skip out on the bill like we’re in some fucking reenactment of Bonnie & Clyde, talking about himself for 3 hours, gorging himself on pancakes, eggs, sausages, and french toast — he asks me for beer money. 

Dear Jazz Musician Ray -

Thank you for providing me with hours of laughs.  I continue to tell your story with incredulity in the hopes that you’ve now made enough with your “craft” to pay for a chick’s Stella without resorting to a life of crime.  Maybe you should save on the Match.com subscription and stick to Craig’s list.  It’s free.  And legal.

xx,

RA

*Names have been changed to protect the identity of the clueless.