Lessons from the Dating Front Lines: New York Edition

I have a confession to make: I don’t always treat men well.

I have a reason for this. More an excuse, really. Before I met ex-Steve, the first love of my life from age 23 until nearly 25, every man I’d ever dated followed the “Rule of Three.”

The Rule of Three was thus: Great first date. Great second date. Even better third date. Then nothing. A few texts, broken plans, messages further and further apart. Then *plop*! Gone. Never heard from again. Might as well be dead.

When Steve broke the pattern of the Rule of Three, and we wound up on a fourth date, followed by a fifth, sixth, seventh, and so forth, I knew it was something different.

But that relationship didn’t last. And while I never pine for the now-married man anymore, that situation and all dating scenarios prior to him took a toll on me. But I certainly learned the lessons of dating in the wilds of New York. The main one? When you find you’re done with him/her, you never have to call again. No explanation or goodbye necessary. Zip-bam-boom. Done. And there I was, always frustrated that they didn’t have the decency to tell me they were no longer interested. I just hadn’t learned the lessons.

After a long and intense relationship, I discovered what I wanted out of my next one, but I was far too exhausted to embark on another serious relationship, so I turned to dating. Just dating. Prior to the aforementioned first real love, I’d only ever politely told a guy that I no longer wanted to see him once. His reply? “Wow. I thought you were really digging me.”

See, I actually told him I liked him. And that was cruel of me. Really I was just trying to convince myself that I liked him. It’s time for me to come out with it: I’m just not nice to men in the end. But I’m working on it! Really, I am.

When it comes to me, I find myself following a “Rule of Four.” Same as the rule of three, only the roles are reversed. Four tends to be the max number of dates, the bonus round if you will. I rarely ever expend the energy for a fifth. Actually, I never have. Which I think is pretty typical.

Whether or not you want to believe me, I’d say seven times out of ten I know a man isn’t The One for me, or even right for me, in the first half hour of meeting him. So why keep dating them, you’re probably wondering. Well, because you just never know. And if nothing else, hey, I had a relatively good time (eight times out of ten), had a few laughs, imbibed a few free drinks–and bought a few rounds myself, of course–and in the end had yet another experience to write about. After all, what’s life if not for a series of experiences? I prefer to make most of mine interesting.

Four online dates later, I deleted my profile.

The most recent experience that got me thinking about my mistreatment of the men I date came on Monday late afternoon. I received an email from Peter, the man I’d been dating before I took my vacation to Alaska. We had a nice time together. I knew almost instantly that he wasn’t someone I would pursue a long-term or serious relationship with, but he was smart, interesting, had some interesting stories to tell, and was significantly older than myself–just my type. He was probably, dare I say it, too stable for the likes of me. Sure, he had a boatload of money, power, and a long history in the upper echelons of Washington politics, but that wasn’t enough for me. If anything, the experience taught me that I could never be a gold digger, no matter how many jazz clubs I was taken to, drinks I was treated to, and cab rides home I never paid for. Ever the chivalric gentleman, Peter just wasn’t the one for me. Unfortunately, he broke my pattern: he sent me an email outright asking me why the hell I had gone “radio silent” on him after I returned from my vacation.

What planet are you from? I wondered. I’ve dated two other men his age and they’ve never cared about the silence. The silence is never brought up. It’s just accepted. That’s dating in New York. Will I still keep in touch with Peter? Like most of the men I’ve dated, no. But that’s his choice, and I’m more than okay with that, truth be told. I told him I really enjoyed spending time with him–I did!–but that I wasn’t going to be intimate with him. “Intimate.” God, I can’t believe I’m at the age where I actually use that term. Nevertheless, his response was succinct and to the point: “I’m not going to waste my time.” The man is looking for a partner, a mate. He doesn’t want to spend time with someone he isn’t going to get down with. Well, okay then. That’s that. At least he thanked me for being honest. I suppose I should say the same of him.

I almost never have to have these conversations. I don’t even know why I ever bother telling a guy, when and if I do actually tell him I’m not interested, that I still want to hang out and be friends. Who are any of us kidding when we say that? We’re dating because we’re attracted to each other. And if we aren’t, one or both of us say sayonara. This whole friends with the people you’ve dated thing? I can’t. I just can’t. There’s a reason we didn’t work out. Let’s just leave it at that, yeah?

In an attempt to halt a ramble that could easily continue for another two hours if I allowed it, I’d like to take a moment to reflect on the men I’ve gone on dates with in the last few months, and how each ended.

DB from first dating site I signed up for as a joke: one date. At the end of it, he texted and said he thought it went really well but sensed I didn’t feel the same. (Right, because he was a total jackass so full of himself I almost jumped out of the cab at a stoplight…seriously.) I told him he’d really have to impress me to get a second date, and that was that.

Dude from other dating site: Nice enough. Kind of vanilla. Not much of a talker. Got a text asking for a second date. Never responded, never heard from him again.

No love for you

Cat-obsessed jazz-playing dude from same dating site: Awesome conversation, talked a lot about our cats. Super cute. Blonde. Cute glasses. …. 5’5″ to my 5’8″. Awkward. Two dates. Super awful for me to have to bend down to kiss a guy. One kiss. That’s all he got. Stopped responding as often as I used to with texting. He was a bit overzealous with the texting–something I notice with a lot of us cat people. Finally told him I wasn’t interested in dating him after the third time I turned down a date. Never heard from him again.

Jeff from Jersey, same dating site: A fun, flirty situation. Busted each other’s balls a lot–I liked that. But he tended to be a little too harsh with some of his digs. There’s a difference between teasing and insulting. I like to walk the line, this guy liked to cross it. Last date was Halloween. He took me to a party at a colleague’s apartment. When he wasn’t being an outright jerk to most of the girls, primarily just insulting them, he was standing in the corner and trying to get me to come over and make out with him. Meantime, I was thoroughly enjoying all of my conversations with the people I’d met that night. Great party! Actually, it wasn’t, but you have to make the most of your situation, don’t you? I had fun. After we parted ways, we never contacted each other again. Plus, he almost made me bleed a few times biting into my lip. Foul.

Crush: This lasted a while, and I wrote about him a few times on this blog. Lasted, secretly, from about September ’10 through mid-February ’11. Didn’t work out in the end because it turned out he was a complete liar. My last words to him? “F**k you. Have a nice life.” Did I mention this was over text? …. I should also mention that he’d promised he’d always be open with me…and then made up excuses for almost an entire month after seeing me about twice a week since everything started. Yeah, I’m no dummy when it comes to these situations. I called him out on it, and ended things straight away. We haven’t spoken since (despite his claim several months prior that, “If this doesn’t work out, I’d still want to be friends with you. Because you’re awesome). Whatever, buddy.

The Professional Chess Player: We met randomly in a bar in the meatpacking district on a random night where Lindsay and I just decided to go out. We met some interesting people that night, but no one worth pursuing as more than that fifteen-minute single-serve friend. Bored of the first place and not ready to go home, we walked into another club down the street. Dressed in a pair of my highest heels, I met a tall, bald man. I love the big Mr. Clean types, and this guy fit the bill. But it was dark in there, too. Well, I’d give him a chance. Ninety-nine percent of the time, I don’t meet men in bars or clubs, and if I do, there’s very little chance I want to go out on dates with them. No thanks, pal. But this fella intrigued me, so I gave him my number. It was three weeks later that he called me. I was flattered–but nervous, too. All I remembered about him was the Mr. Clean type. Okay, tall hot bald man, I’ll go out with you. I was impressed that he suggested tea on a Saturday afternoon for a date. Certainly not the typical sketchy guy you’d usually meet in a bar. Even the nice boys always offer to take me out for an evening of imbibing alcohol. But from the second we met up, I wanted to go home. Relax, I tried to tell myself. Give the guy a chance. Oh, no. The man had only ever had one cup of coffee in his entire life. All he could talk about was chess. And his talking down to me about nutrition? Oh, fella. You’re a nice guy and all, but you’re not getting a second date. Poor guy called me four times over a month after that. I never once responded. Usually they get the message after the first ignored attempt at contact.

And then there was Peter. Probably the first good experience I’ve had with a man in a long time. Certainly in the last few years of dating.

I saw something on the morning news the other day that listed the top five best cities to get a date. New York was in there. Sure, easy to get a date. But a date worth going on more than a few times? Good luck finding that…unless you’re a romantic settler. I guess I’m just too restless for that. I’d rather be writing.

I suppose I’m not mean to men after all. In fact, I’d say that I’ve just simply learned the Dating Game. Once you decide you’re done, up until four dates, it’s fair enough to either never talk again, or to at least end it over text message or email. If one of you doesn’t get that? You clearly still need to learn the laws of the this land.

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5 thoughts on “Lessons from the Dating Front Lines: New York Edition

  1. Not bad Lorrie. It’s nice to understand the other perspective. That said as a guy who’s been on both ends, I (and I expect most guys) genuinely appreciate getting that clear and direct message rather than the woman disappearing into thin air. And because I know I appreciate it, I do the same for the person I’ve dated if I chose to stop seeing them romantically.

    Also I realize this is purely based on your experience but don’t think it’s true that you can’t become friends after starting off dating – there’s a level of maturity that needs to be there (for both the person ending the intimacy and person being told). Actually one of my semi-good woman friends is someone that I first dated. A couple months ago I went on a couple dates with a very nice, cute, smart woman – was on the fence after date 1, went on date 2 and pretty much had a not so great time, decided that was it for me. I called her and offered the whole friendship thing and while we haven’t hung out we keep in touch I suppose and I don’t get the feeling either one of us is opposed to doing something together if the opportunity came up.

    More recently (as in this past weekend), a woman I went on a few dates told me basically what you wrote in there – enjoyed the time blabla but we should probably just continue being friends blabla. I totally respect it and don’t see why it’d be a waste of time. I actually enjoyed the person as much as I was attracted to them, but that turns off once you tell me you’re not attracted towards me. Why would I invest any emotion otherwise? Doesn’t mean I think that person sucks, because clearly I didn’t just means I am okay with making friends out of the experience. Maybe this is different since she had hinted towards wanting to go out a few times within the past 4-5 months so we had sort of an established (not friendship) but relationship of some sort before.

    Anyway there’s my 2 cents. I should read your blog more often, interesting stuff. The subject line caught my interest.

    PS: we need to have Thai again PRONTO

  2. I disagree with this game. I think it’s rude of guys to just stop responding when they decide they’re no longer interested. How hard is it to send a simple text saying “I don’t think this is going to work out.” and save the other person a few days of wondering before it sinks in. If, after the initial text, they still don’t get the hint, then sure…ignore the crap out of them. But I still believe in basic human decency and treating people the way I would want to be treated. And I know I hate when guys go from interested, flirty and all over me to a vanishing blur in the span of a day without any explanation. I have no interest in playing dating games, especially if the rules require me to be rude to someone.

    That said, people do what they want to do and ultimately life goes on. Sons day I’ll meet a decent guy who doesn’t disappear and you’ll meet a guy who breaks the Rule of Three again but sticks around this time and neither if us will have to worry about this bullshit game again.

    Dating sucks! This is why Netflix is so popular.

    • I know you hate this game more than anyone I know. I used to feel that way, too. I have never once had a guy give the courtesy to say “hey, I don’t want to date you anymore.” Hence where I learned. Also I think I often just find myself in that “oh, yeah, we both realize it’s done” situation. Oh well.

      • I definitely think if you both have the realization and it’s obvious, it’s not so bad to leave it without going back in just to have the awkward conversation. That’s what happened with me and Dave (the guy I was dating while you were dating your silver fox). He revealed his uber-religious side in what resulted in a really awkward conversation and I basically left with the thought in my head that this was over. And the look on his face said he knew it. So I told myself I’d let him contact me, since I didn’t want to call him and get his hopes up thinking I wanted to keep seeing him, and if he didn’t make the effort to get in touch with me, I’d know he knew it was over. He never texted, so…

        Also, sorry if any of that last comment came off sounding rude in any way. I was posting it on my phone while doing other things, and I wasn’t sure if the tone conveyed came off mean or rude in any way. So I apologize if it did.

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