Dating Question

I did a quick count. Unless I’m forgetting some, it’s probably around 25.

I had to stop and think about this one. It’s subjective. I don’t know if I ever relax. I don’t know how much laughter counts as “a lot.” I hate fake laughter. I tell stories that are interesting and amusing to me, but a few years ago someone had to stop me and explain to me that I was talking like a professor delivering a lecture, as I spoke in paragraphs.

How many dates must one have before one has “dated” someone? Depending on how you define dating, it’s either been “none” or … two? Three? I was intimately involved with a woman for the better part of a year, but we were not technically dating, as during our long period of getting closer, we learned that she wants kids and I don’t, so when we crossed our proverbial boundaries, we knew that things would end as soon as someone else came along.

It doesn’t really matter what definition you use. It’s fantastic you got over your depression, so I don’t mean to make you feel bad about that at all. But ask yourself realistically - when you were depressed were you somebody that anyone would want to date? If you weren’t, I don’t think it’s fair to yourself to count those dating failures against yourself. You had a problem, it probably made you a pretty unappealing date, but you got over it and now you’ve dated just a couple women since then. That’s not many at all. Keep trying.

I don’t think you should fake laugh. Be yourself.

There was a poster here, until he got banned, who speculated that he’d do better dating when he was older, because young women wanted to go out and have fun and he didn’t. That poor guy is in for disappointment, because almost everybody likes to go out and have fun. My mom is 60 and if she met a new guy who never wanted to actually do anything she’d be really disappointed. I love that I’m 30 and I don’t ever have to pretend I like staying out until 4:00 AM listening to loud music and drinking again, but I still like to relax and have fun and so does my girlfriend.

It sounds like maybe you’re a lot different than that. Do you actively target women who seem to have a similar mindset and temperament than you, or do you go after whoever?

Out of curiosity, how much do you enjoy your dates? I’m not asking you to evaluate the women themselves, but how do you find spending an evening with a new woman when she agrees to go out with you? Is it really enjoyable for you?

If you went out with a woman who was educated, had a good career, didn’t drink, but her temperament was bubbly and fun loving and not at all professorial, would you enjoy having dinner with her?

Quite right, but the rejections have continued. That’s why I haven’t dated many.

I am a bit older than you, and I would love to stay out quite late enjoying loud music, provided it’s coming from a real band, and without any expectations of drinking and/or dancing.

I usually have enjoyed them, because even if the event isn’t much fun, I’m incredibly excited by the possibility that maybe it will be different this time, that I’ll finally have the girlfriend I’ve wanted for about fifteen years, that maybe I’ll no longer be a dateless loser, that I’ll actually feel someone touching me in a good way, etc.

I’d be a little embarrassed at having similar levels of education but no career, but as for her personality, I have no idea. Maybe.

One day, when I was a miserable undergrad, a female classmate and I were walking after class, and she asked me “what kind of girls do you like to date?” Besides the erroneous terminology (I was over 18, thus we were talking about women, not girls), I had trouble finding the words to convey that I can’t answer the question, because I don’t get dates.

You sound like a fun guy to me.

I can certainly empathize why why you’d feel that way. But doesn’t it sound a little bit untargeted? You won’t have the girlfriend you’ve wanted for 15 years. You’ll have a girlfriend, which you’ve wanted for 15 years. As you said, you don’t even know what you’d want in a girlfriend. On the one hand, it’s hard to imagine someone feeling like you’re genuinely interested in them if you aren’t even having fun, but are excited at the prospect of being with anybody. On the other - I don’t mean to be hurtful - but doesn’t what you said sound really desperate? Do you know anyone attracted to desperation?

Since you obviously can’t take a lot more rejection anyway, why not think deeply about what you’d actually want in a partner and seek that out? You should be excited about your date, not excited about the possibility of being with anyone.

You’ve been wanting a girlfriend for 15 years, you must have imagined an ideal girlfriend, right? In other words, do you honestly have no idea who you’d like or are you saying you have a hard time putting it into words?

What do you value in a friendship? Are there any fictional women you’d find appealing? Can you identify what it is you like about them?

Are you serious? I mean no offense, I really can’t tell sometimes.

That’s what I meant, actually. I do know what I want in a girlfriend. The first time I fell in love was in 2002, and though we weren’t technically dating, it was close enough for me. I knew I was interested before we ever met in person, after I called her and we talked for over an hour. I have been looking for that feeling again, of being so electrified by someone’s intellect as we banter. If I don’t necessarily encounter that specific phenomenon in someone, I can still find other attributes attractive, and, though I was late in understanding this, short-term relationships can still be positive and successful.

I was in love again about a decade later. That’s the relationship I mentioned earlier. I’m close friends with both women now.

Yes, and yes: me. I think I would find it refreshing, since I am desperate also. I won’t be judgmental.

Yes. Loud music isn’t necessarily a great first date idea because the noise can make it impossible to talk and get to know one another, but most women would love going out and listening to live music. You had me worried you were too serious to have fun, which is a crucial part of dating.

Have you ever tried joining a book club or something similar? It’s a great way to meet people with a more developed intellectual side. I used to go to one that was specifically for young professionals… I suppose if you showed up to any random book club I guess it’s likely there’d be a lot of women in their 50s and 60s. Maybe has one?

Also - I did speed dating once and loved it. I wished I lived in a larger city and could’ve done it more often. If you click with someone it feels like it’s over in 10 seconds, and if you don’t it drags on and on for 5 minutes… but how bad could 5 minutes ever be?

So she’s sick for a week but still going to work. After that I’d want to just crawl in bed when I got home. I wouldn’t assume that was a brush off but then I’ve never dated women. Guys are easier. if they don’t want to see you again, I’ve found that they usually say so. I don’t envy the song and dance routine you straight guys seem to have to go through.

I’ve almost never had the opportunity to do it in that context. I would need to meet someone who is willing and able to attend the same show, at such a time that tickets are still available, and all that. Even so, I might still be too serious (and misanthropic) to do what others call “having fun.” There are a few things I suppose I like to do, but I don’t know if I’m really passionate about them. There are things I think I am passionate about, but they’re not appropriate topics of conversation in a “fun” context.

I have signed up for several meetups (one of which enabled me to find out about, and get a discount to, the speed dating), and I rarely feel like I have the time or inclination or means to attend their events. It does usually seem like the attendees are older, and/or I’m not really interested in the events. Specifically regarding book clubs, the problem there is that I have a lot of other things I want to read, and I don’t want to spend all my reading time fulfilling obligations (by reading things I don’t want to read) to a group I’m only in for the purpose of meeting people. I’m in a similar (non-meetup) group now, and I’ve come to dislike it, and dislike the people involved.

I am obligated to spend my time trying to get a career, ponder working on music, and take care of myself, along with recurring political activism. I find it difficult and stressful enough to try and do all the things required just to keep myself healthy, functional, and solvent day-to-day. Going to far-off dinners and such with a handful of people who probably aren’t the sort I’m looking for just doesn’t seem like a good idea.

Yeah, I’m going to do that in a few hours. I’m intrigued.

I didn’t date much in my early 20s because I was starting and then running a business and take care of a dying father. At the time I wasn’t sure if it was a legitimate excuse or just something I was telling myself. In hindsight it was totally legitimate - I don’t see how I could’ve met more women given what I had on my plate. I didn’t have money, I was tired, and I spent all my time in my office with people I couldn’t date or taking care of my dad.

So I totally get not being excited about spending the little time and energy you have truffle-hunting for dates, but on the other hand I don`t know of any other way to meet people. I think most adults find it an arduous task to meet new friends or lovers. You’re just trying starting establish yourself professionally, right? Maybe you could become a kindergarten teacher and date all your colleagues.

Good luck!

“I find nothing in her actions to suggest she’s just afraid to tell me (she even said on our first date that people who aren’t honest about not wanting to go out are just assholes).”
Your naivete is endearing and touching.

That was pretty interesting. I have a good feeling about it, but the attendees cannot contact one another until we get a link within 48 hours, so it remains to be seen if anything will come of this.