He’s Just Not That Into You…

Yeah. I pretty much hate dating. Relationships and partnerships I’m totally cool with, but dating? All that confusion and craziness? Where there’s always one person that likes the other person more? I would rather not.

In my 20’s dating was fairly easy – and I wasn’t even trying too hard. I had crushes, yes, that didn’t like me back – but that was no big deal (sometimes that’s the purpose of the crush – just to crush).  For a while I pretty much just dated every guy I was interested in. I liked people, and they liked me back. I guess I was just extremely lucky in that respect.

I’ve been in love about four times. I’ve had some amazing relationships with some awesome people,  despite the fact that we eventually realized that things wouldn’t work out between us. But now? Now dating is pretty much like pulling teeth. It’s miserable. That’s why I say that I wouldn’t wish it upon my worst enemy…

Back in the day, there were a good number of guys that I’d be interested in dating. They were friends, friends of friends, or just guys that I met on the street. Since my last break up, however, I would say that I’ve found about…TWO guys that I’ve actually considered having a relationship with (in retrospect, only one of them would have been a good candidate because the other one had problems). Beyond that, I’ve seen just ONE guy around my age that I’ve found attractive (men, in general, just don’t age very well…).

Back in the day, no one played games. It was simple.  We both showed interest and put in effort. The rest was history. No game playing, no hesitation. We were open about our feelings and made things happen. Perhaps that was because I dated the “nice guys”. I didn’t date womanizing men who thought they were the shit, who played hard to get. Who, if you showed too much interest, thought you were “clingy” or “too easy”.

So I’m supposed to hook a guy in by demonstrating a lack of interest? That sounds pretty counterintuitive to me. If I a person acts a bit stand-offish, why would I want to pursue them? I’m much more interested in men that show that they’re down for me. I’ve been told that many men tend to enjoy the chase and see dating as a feat to accomplish, a game to win. I just don’t get how that works. AND, for better or for worse, I’ve just never experienced that kind of (wack ass) behavior before.

Dating in my 30’s – it’s like going back to school to learn how to how bad and fucked up men can be. I lucked out in my 20’s. Now I’m left with all the “leftovers”. By now, most of the men who are good looking, responsible and caring – THOSE guys got snatched up by their late 20’s (or early 30’s) and are now married or engaged to great women.

The rest of the guys that are single in their 30’s or 40’s? They tend to be of three types:

1. The ones that just want to hook up or date casually, who think they can be playas for the rest of their lives (not realizing that eventually age and undesirability will probably catch up to them).

2. The ones that you’re not attracted to (for a multitude of reasons)

3. The ones that have severe emotional BAGGAGE (many of whom are trying to get over an ex).

There’s also a rare fourth category of:

4. The winners that broke up or got divorced in their 30’s and 40’s

Those of the 4th category are pretty hard to find because you don’t tend to see them at bars or clubs. Oftentimes those ones get snatched up pretty quickly too.

* * * * *

I guess, since I had lucked out before (all the guys that I liked, liked me back), I don’t get why NOW, men who once seemed interested in me suddenly become disinterested in me. What happened? What did I do?

Case Study #1: “The Professor”

I met The Professor on an online dating site right after I broke up with my boyfriend of 6 years (the relationship ended when I entered my mid 30’s). We had an awesome first date. He seemed to really like me…or so I thought. After a month or two, however, I realized that he wasn’t responding to my text messages right away. He began to cancel dates. I didn’t understand. When I asked him what was up, he said vaguely that he didn’t know what was going on, and that he was going through some personal stuff. But the exact day after I told him I wasn’t going to talk to him anymore – that was the day he asked me to hang out with him. And, being totally interested in his attention, I took him back. This happened a few time before he finally moved on to another ex-girlfriend who was, in his words, “very pretty but kinda dumb”. So it goes.

In retrospect, The Professor fell under category #3: Men with baggage (he definitely wasn’t over his ex, and he was clinically depressed).

My Case Study #1 lessons learned:

— Older people (with much more dating experience under their belt – including myself) tend to pickier. Before, if we saw flaws, we just saw them as things we could work through over time. Now when we see flaws in potential dating candidates (no matter how slight), we tend to see them as deal-breakers or barriers.

— Why didn’t The Professor like me? Part of it was due to cultural differences. He said I was “snarky” (I shouldn’t have playfully teased him so much) and that I “made him think too much” (engaged in intellectual conversations), when he just wanted a sweet and pretty girl who didn’t challenge him (and his weak ego) so much. In fact, that latter description is the girl that he married last year.

Case Study #2: The Youngin’

The Youngin’ used to have a crush on me when he was in his early 20’s. He’s in his late 20’s now, and since I’ve become single he’s been hitting me up to hang out. Well I finally went out with him a few times, and eventually we hooked up – a few times. He said he had a really good time, and so did I.

Afterwards, however, he was hesitant to hang out with me. I kinda don’t get the “hit it and quit it” philosophy. If it was fun the first few times, why wouldn’t you consider doing it again (even if he doesn’t want anything serious)? We both agreed that we were just down to have a good time. Was he afraid that I’d get attached to him? Was he just over it now that the goal has been achieved? Did he have some personal baggage to deal with which prevents him from getting more involved? Was he more interested in someone else?

And…I know I’m not everyone’s cup of tea, but I kinda don’t get why not.  Maybe I’m confused because guys like him would have totally been interested in me before. We have a lot of things in common, we both find each other attractive. The biggest thing is our age difference and where we are in life. I’m looking to settle down, and I’m a good amount older than him. Does he think that I’d want to get too serious too quickly?

And then I wonder: would he really spend all this time (sporadically over the past two years) trying to get at me if he only wanted something a few times? Ferrealll? That’s a lot of effort for not a lot of gain, IMHO.

My friend Roy says that there’s two reasons why men only want to hook up:

1. Because they just aren’t that attracted to your personality (you lack certain desirable qualities or have too many negative ones)

2. Because they don’t find you that physically attractive – or they think they can do better

That doesn’t mean that those feelings won’t change over time (they can), but for the most part, all a guy knows right now is that he’ll have sex with you. The rest…only time will tell.

Of course, there’s also the guys that are cheating, and the guys that aren’t ready to settle down, but we’re not counting those here. However, I’ve heard from many guys that if they don’t want to commit to you, it’s more about YOU than it is about THEM. Sorry, but it’s usually true. If a guy finds someone that they’re completely nuts about, they’ll probably lose their playboy lifestyle and will commit pretty quickly…

My Case Study #2 lessons learned:

—  Be more attractive?

— Be clear that you’re not going to become clingy to put them at ease.

— Um fuck it. If they don’t like you, you can’t really convince them. What can you do? Become a different person?

* * * * *

There’s another one or two guys who (while I’m not very into them) I’m kinda surprised that they’re not interested in me. We all hate dating in our 30’s and find it hard. We have a lot in common. We’re friends (or acquaintances). What about me makes them disinterested?

On the flip side, there’s also been a number of guys who’ve been really into me, who have pursued me. Unfortunately I just haven’t been that into them.

AND…to complicate things further – I give a lot of people chances that maybe I shouldn’t. Sure I like 50-60% of them, but there’s a good 20-40% of them that I can’t stand (the leftover percentage is made up of “tolerable” or “neutral” things).

I guess the biggest burn in the end is that there are a number of guys (guys who I don’t even like that much / guys who are just okay / guys who, in my 20’s, I would have NEVER considered dating) – that are rejecting me, while I give them a chance despite my misgivings about them. I know my dating options are limited, so I try to stay pretty open-minded. Sometimes that’s what bothers me the most. I’ve given them a chance, but they wouldn’t do the same for me. I don’t know what that means – should I be less open and more discriminatory too? Only time and experience will tell…


Edit: After writing this piece, I ended up having a couple of months of good FWB sex with the Youngin’. And I did start hanging out with one of the two guys that I thought wasn’t into me. Perhaps not all is lost…


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