third time is not the charm

A few weeks ago I had three "dates" in the span of one weekend, with women who, coincidentally, all live in my neighborhood:
Friday night with a cute law student named Cathy; Saturday with a sexy singer/songwriter named Rita; and on Sunday, it was the lovely Denise, a marketing analyst (I think). And they all ended badly.

Cathy and I met over drinks at one of our local bars and hit it off from the get-go. She was smart, attractive and quite opinionated.
I didn’t have a problem with the latter until she started ragging on people with children at length, and made it clear she wanted none of her own. OK, so not girlfriend material for me but she was quite the hottie, so I figure if I play my cards right, I’ll get some sex out of it. Nope.

We finish our drinks and go for a late night snack at a nearby 7-11, where she proceeds to pig out on a couple of cheese dogs.
Fine by me; I love a girl with an appetite. I then walk her home and as we stand in front of her building, we kiss. Cool.
Then, she drops the bomb:

“I think you should know that I’ve been in an on-and-off relationship with someone I’ve known since we were six.” (She was 31.)

Great.

She goes on about it, implying it's currently off, but there's major ambiguity there. So, I throw in my two cents.

“Listen,” I said, “I’ve been in a similar dysfunctional situation with someone for two years now, but I’m looking forward to extricating myself from it as soon as possible. And I think you should, too.”

(Of course, this must’ve been the alcohol serving as my spokesperson, because although what I said was true, there was no reason for me to bring it up with a woman I clearly had no intention of considering for a serious relationship. Or was it my crotch doing the talking?)

“Yeah, I guess.”

So much for Cathy.

+ + + + +

I invited Rita to a show at a new concert venue in the neighborhood. She had to take care of something immediately before the show,
so we decided to meet inside. There we met up with friends of mine who were acquaintances of one of the singer/songwriters on the bill. Rita, on the other hand, was known to the evening's headliner and was interested in seeing him perform. In between sets, after she met my friends and they’d gotten all chummy, Rita was asked why she’d been late getting there. She told a boring and convoluted story that had the unintended (?) result of alerting us to the fact that SHE LIVES WITH HER EX-HUSBAND. The night's positive vibe kinda quickly dissipated after that.

At one point, she excuses herself to go to the ladies’ room, and I’m bombarded with questions regarding my prior knowledge of Rita’s domestic situation, by friends who are quite upset.

“I didn't know 'til now. But I could sense there was something weird going on,” I replied. “When we met, at one of her shows, there was this dude hovering around who seemed like more than just her personal assistant. However, she was flirting with me and accepting my invitation to go out, so I kinda put it in the back of my head. But it kept nagging at me 'cause I just couldn’t quite put my finger on it.”

At my insistence, we left halfway thru the headliner’s set and I told Rita I was bailing on another show we’d planned on going later that evening, also in the neighborhood.

“I’ve had enough for tonight. I just want to drink.”

“Well, I’m driving and I’ll take you anywhere you want to go.”

"How ‘bout back to my place so we can have some angry sex?", I thought. I settled for a bar nearby.

What Rita failed to mention was that her ride was a late-model Mercedes. All of a sudden, her living with the ex made me feel even more uncomfortable. Not because of the car itself, but because it made me think of whose money was possibly behind it.
And all the different scenarios I came up with in my head felt really weird.

She drops me off in front of the bar, and before I get out she profusely thanks me for the evening, hints at some personal issues she's dealing with, and promises to get together soon. She then leans in closer, gives me a kiss, and drops the F-bomb.

“You’re such a good friend.”

Now, I really needed a drink.

+ + + + +

I’d been introduced to Denise by a mutual friend and neighbor late last year. I subsequently ran into her a few times at a local bar, but failed to notice until months later that she was a girl I’d been matched with online; one who I’d contacted but never heard back from.
I should’ve left it at that. But no, Mr. Looking for Love had to take things a step further. Ugh.

I meet her at that same local bar after she’d been partying earlier in the evening with friends out in Manhattan, and tell her about our online “past”. She apologizes for not responding and gets a little apprehensive at first but, ultimately, gets a kick out of the whole deal. But after a few drinks I notice Denise begins to get slightly incoherent and even a bit antagonistic, which is quite likely due to the alcohol being coupled with the copious amounts of weed smoked with her Manhattan friends, leading to her lovely chemically-induced makeover.

Now, I for the most part don't have a problem with whatever party favor gets you thru the night. But if what you regularly consume and enjoy leads you to becoming a subtler version of The Hulk with lip gloss, um, no can do.

I decide to call it a night. Who’s got time for a 34 year-old frat girl? Not me, anyway.

hookers are starting to look pretty good

On a relatively mild Friday night in early December '07, I went on a date with Corinne, a 26 year-old paralegal from Ohio who had shown interest in me the few times we’d bumped into each other at the bar where my buddy Mark works. I’d asked her out a few days prior to the date but had not heard back from her. Just as I am about to write the whole thing off, Corinne e-mails and asks if we’re still on for Baraza, a Brazilian hotspot in the East Village I’d told her about. So, I’m back in that headspace, and on the night of the date I get decked out in a new shirt and jacket, looking really sharp.

We went to Baraza and had a great time. We flirted, we talked about life, love, the possibility of pursuing a relationship, and most importantly, we grinded into each other as we danced; couldn’t have been more promising.

We left after last call, got a cab and Corinne proceeds to snuggle up to me on the way across the bridge to Williamsburg, where she used to live and had her car parked—she was currently living deeper into Brooklyn—and called it a night. Since she was a bit tipsy and was going to drive I offered to ride home with her and catch a cab from there. She declined. We said our goodbyes and I continued on to my place in the cab. When I got home I called to make sure she got home OK. I got voice mail and the mailbox was full so I called the next day, spoke to her a bit. She mentioned she was too busy with work to see me before Christmas and we left it at that.

Four nights later I’m at a neighborhood bar drinking with Mark who asks me what I’ve been up to. I tell him that with the exception of the previous Friday I’ve been staying home. After I tell him about my date he mentions that CORINNE WAS AT HIS BAR AFTER I DROPPED HER OFF. She met up with this guy Dan who hangs out there also—who’d called her while we were at Baraza, by the way—and…man, did I feel like an idiot. I manage to not let it diminish the rest of my evening—I ended up making out with Nancy, a cute bartender who works elsewhere in the neighborhood—but the next day, when I wake up, I’m pissed. Ah, that familiar feeling!

Corinne is asking me to be patient with her and thanking me for not wanting to just jump in to bed with her and meanwhile she pulls this bullshit?! Did she think I wasn’t going to find out she’d been at my friend’s bar?! During his shift, no less?!

Later that morning I send her an e-mail simply asking “Just out of curiosity, where you at Mark’s bar Friday night?” To which she replies “Yes, I went there for a nightcap. Why do you ask?” WAS SHE KIDDING OR DID SHE THINK I WAS STUPID? My response is, “Wow…I feel like an idiot” and leave it at that.

Once again the story is the same, the names just change: I went on a date with a girl I really liked, who managed to disappoint, as usual; and two nights later I was having sex with a woman I couldn’t get out of my bed fast enough. Who then wanted to watch The Simpsons afterwards. (Didn’t she have a TV at her place?)

I was tiring of making an effort with women who ended up not being worthy of me or any righteous dude. And I’d also lost most of my post-coital patience with women I had no emotional attachment, so…I once again started contemplating going with hookers. Seriously. Quality call girls, of course. No drama, no bullshit and no watching The Simpsons on the couch after we’re done.

I wasn’t joking.

But the Corinne story did not end there. Oh, no.

I’d planned on leaving things the way they were after I found out what happened that night after our date. But a couple of weeks later I run into her and was caught off guard when she approached me at Mark’s joint wanting to apologize. I was interested in what Corinne had to say about ditching me to come back to my own neighborhood and hang out with some other dude, after—concerned about her inebriation—I graciously offered to go way out of my way to make sure she got home alright.

I listened intently to Corinne and what I got was a rambling, off-topic, self-serving attempt at an apology that had nothing to do with me and was all about assuaging her guilt.

So I let her have it.

“Can you imagine how foolish and idiotic I felt when I found out that instead of you being in bed, you were 3 blocks from my apartment drinking and who knows what? And when I asked you about it, your answer was priceless: ‘Yes, why do you ask?’ Are you serious? How would you feel in my shoes, Corinne? Listen, I’m not your boyfriend and you may not owe me any explanation, but how ‘bout some common decency? I think you’ll agree that after our conversations about going on dates and getting to know each other and you asking me to be patient with you about sex and whatnot, after the physical proximity we’d had, I had an expectation of courtesy on your part. Obviously, I was wrong.”

She was dumbfounded. I was just getting warmed up.

“So, yes, I got upset and had thoughts of getting you to sleep with me and then crudely ditching you. That was my little revenge sex scenario. Because, let me tell you Corinne, what you pulled that night is the kinda shit that turns nice guys into assholes. Seriously. But I thought better of it, nipped it in the bud, and chose not to call you again. I put it all behind me. And now, you come to me with a clueless pseudo apology, in which you either don’t even know what you did or or think you did nothing wrong that night. You sound as if you’re apologizing about something else, like not calling me recently or something. Frankly, either way, the end result is that bitter taste in my mouth all over again. And having to rehash nonsense that I’d already put aside.”

I was on a roll and she had that I don’t dare interrupt him look. Pretty smart on her part. For once.

“Luckily for you, I’m a mellow dude and just walk away from these situations. Even humiliating ones like this one. But many other guys deal with being treated like a fool in a much more belligerent way. You might want to think about that the next time you take a nice guy for an idiot. OK?”

“Um, OK. Sorry.”

And with that, Corinne sheepishly went back to the table she was sharing with some friends. As I finished my whiskey, I started wondering about the call girls I was too chickenshit to contact.

I've bumped into Corinne a few times since then, and she always says hi with a look that says Please don't slap the shit out of me; I won't do it again. Not to me she won't. Heh, heh.

legalese

Sylvia—a cute, blonde lawyer in her early thirties—was another girl I also met online. After a few e-mails we made plans to meet up for drinks on an early Thursday evening. I had already decided to play it cool and show up fifteen minutes late, to cover up the fact that I was slightly nervous. As I'm waiting in front of my building for a taxi, and just as it's pulling up, my neighbor—and occasional hookup—Celia appears with her dog. I didn’t say where I was going, but I was waiting for a cab, smelling good and slightly well dressed…I was pretty sure she’d figured it out.

The date was a success. Nothing special, but we laughed, talked, had a few drinks, and really enjoyed ourselves. Standard good date material. It lasted some 3½ hours and only concluded at that point due to Sylvia having to be in court the next morning. Afterwards, on our way to the subway, we hold hands, and half a block before the subway, under a tree, in an unlit part of the block, we kiss. It was nice. Kinda romantic, you might say.

We get to the station and I ask her if she wants to get together sometime this weekend—in a previous conversation to set up this date she’d said she had plans on Friday but was free Saturday and Sunday.

“I’ll have to check.”

But I thought you said you were free…

“I know, but I may have made plans.”

Oh, ok…

“No, I’m not trying to be evasive. Let me check. We’ll talk or e-mail tomorrow anyway, so…”

What the fuck was that about? Was she tipsy and didn’t know how to react? Did she feel pressured? Did she not feel a physical connection, despite the kiss? Anyway, we get on the train, talk some more, kiss briefly twice and mutually state how much we’d enjoyed the evening and how glad we were that we’d done this. My stop comes first, we say our goodbyes and since I’d had about 5 whiskeys and had to work the next day, I went straight home, had a bite and then to bed.

The next morning there was a note under my door. It was dated from the night before so I may have not seen it when I got home.

Guess who?

Miss Celia wrote me a three-pager—complete with a drawing of her dog at the end—in which she states “with respect and love towards the wonderful human being” that I am, her desire to “remain good neighbors and acquaintances, rather than attempt to be real friends or friends with benefits”. Let’s see…this was the second time she’d had this ‘talk’ with me. The last time I ended up going up to her place and having sex. Of course.

I start thinking that blowing her off two nights prior night—she wanted me to come up and have sex—coupled with seeing me on my way to be with someone else may have set her off. Whatever…

Meanwhile, I didn’t call or e-mail Sylvia. I wasn’t going to chase after her having gotten “Let me check” the previous night. Granted, there was also the possibility that I may have come on a little too strong. Which was another reason for me not to call. When I finally do hear from her, days later via e-mail, not only was she not interested in a second date, but from her account you would think we’d been on two different dates! WTF?! So, suffice to say, that was that. (Come to think of it, why would anyone date a lawyer? You don't want to break up with someone who has that kind of legal know-how trying to mess with you out of spite, now would you?)

As I take stock in my recent dating letdowns, I start contemplating the possibility of resorting to hookers if this nonsense continued. (CraigsList, are you calling my name?) Nothing too expensive, but I'd make sure they’re hotter than the slightly skanky looking ones from that HBO show about the Bunny Ranch in Nevada. Bet on it. Ha!

fake boobs and cold feet

In the summer of '03, I started exchanging e-mails with this girl I met thru an online dating service. I was wary at first, since she initiated contact without a picture on her profile; always a bad sign. Sensing my trepidation she e-mailed me some photos and my apprehension immediately disappeared: Lina was smart, funny, witty; half-Colombian/half-Sicilian; a music and film geek; and gorgeous, to boot. After our first date we became inseparable. I would visit her and be there for 8-9 hours at a time. Phone calls routinely broke the 5-6 hour mark. I'd discovered the sweet, affectionate, sexy, side of her and was so hooked. Still, I was a bit cautious; but it felt really good to be with her. We had an intense level of honesty going: everything from family, past romantic experiences to money and sexual preferences, was covered in an extensive and frank manner. (Except for one thing: I subsequently discovered she had fake boobs, which she never really came clean about. A bummer, but hey, nobody's perfect. Although her chest was. Heh, heh.)

I never pressured her for anything and we only became physical when I felt she was comfortable. So, aside from getting to know each other better, the one thing stopping us from jumping into a relationship was our respective skepticism: Lina was tired of men not being there for her emotionally—which I like to think is the opposite of yours truly—and I was not looking forward to another dysfunctional, clueless woman with money issues. And when we discussed these things, our responses to each other were invariably, "Who are these people you involve yourself with?!"

It was very, very promising. But still...

Guess what? Lina got cold feet.

One night Lina shows up at my place and from the outset I can tell something is wrong. I just knew it. Sure enough: in a nutshell, I got the "I can't get involved right now, let's be friends" speech. I was literally at a loss for words. Finally, after what seemed like an eternity, I recovered my linguistic capabilities.

"How can you go from fantasizing about me to wanting a platonic relationship in less than 24 hours?"

She said something about thinking things through, deciding she wasn't ready and not wanting to be selfish by asking me to wait, blah, blah, blah. I told her I thought it was selfish of her to expect to get those things that she wanted from me without having to deal with the heavy stuff. She cried, asked me to be in her life, to be there for her as a friend. I said I didn't think that was possible.

But what really led to her change of heart was something that had gone down a few days prior.

Lina’s ex-husband was in town for a wedding and she met up with him for brunch. From our conversations I was able to deduce his reappearance—and what it represented—was at the heart of what freaked her out. Here she is feeling so strongly, albeit with some trepidation, about someone new and right in front of her is the last man she felt that way about. With all the unresolved issues that come with it. So she freaked and bailed on me. ‘Twas that simple.

Back at my place, we eventually mellowed a bit, had the bottle of wine she brought over, listened to some tunes, danced to some Juan Luis Guerra and around 1 am I called her a cab. After I walked Lina downstairs I came back up, got dressed and went to one of my local watering holes. Behind the bar, on a very slow night, Stephanie—who had in fact met Lina on our first date—gave me her shoulder while I got drunk. I got home, fell asleep on the couch and awoke with enough time to shower, get dressed and get to work on time.

While the previous night had left me sad, disappointed and hurt, I woke up the next morning pissed. It was as if I'd gotten a surge of ire instead of a hangover. I was really upset. All I could think of was, I'm too old for this. I'm really tired of mustering up the hope and courage that goes into involving yourself in a serious relationship. Fuck.

I bumped into Lina at an Apple store about a year later and we both purposely ignored each other. I never saw her again.

I sure miss those boobs, though.