Missed the dating boat?

Dear Edahn,

First of all, thank you for answering our questions. I really appreciate the time you put into your responses. I'll try to make my question short and sweet. I was in an 8 year relationship from age 20-28. I was engaged the last two years of the relationship and with every fiber of my being did NOT want to get married. I broke it off and although I was sad and felt bad that I hurt him I was relieved to have my freedom. I gave myself 6 months then started dating. I went out on a few dates then I fell into a relationship rather quickly that lasted 6 months. The guy dumped me pretty hard. He said mean things and completely broke my heart. It was very self-esteem shattering and rocked me to the core. It took me about a year and a half to get over. 

I've been dating now for about 6 years and nothing very exceptional has happened. I've had almost every experience in the book. You name it, it's happened to me. That stuff is funny and good for storytelling but at the end of day it's not very fullfilling. Nothing seems to stick. I just don't seem to find men that interest me very much. I'm tired of this, tired of dating and feel really ready to love someone. The problem is, I feel so old. Like all my lessons came so damn late. Most people are married off by the time they're 33 and I haven't even met "the guy" yet and I'm 36. I guess I don't really have a question but am seeking some advice as how to handle myself. I've just had some great career success and am ecstatic about it but also sad I have no man to share it with. I feel lost.

If I was in your shoes, this is how I would approach things.

First, I would make myself fully available for a relationship. That entails removing any obstacles that could be interfering with me meeting and getting to know someone, as well as being strategic and creative about finding an interesting person. What kind of people am I interested in? Where do those people congregate (in cyberspace or meatspace)? Am I in pretty good shape? Are there some simple things I can do to make myself more attractive? How's my personality? Am I too judgmental? Too reserved? Too serious? Too desperate? What's happening on my dates? I would solicit some feedback from my friends to help answer those questions and start making adjustments accordingly. If this is stuff you're already doing, great. If there's some room for improvement, go for it.

One thing I want to bring to your attention is the story-telling. I have some friends who are good story-tellers. Their frustrating dating life becomes a source of material and their friends begin expecting them to provide some type of entertainment in the form of a frustrating or absurd dating story. I think what starts to happen is that my friends steer their dates in the direction of frustration and absurdity in order to replicate that feeling of surprise and astonishment that they later share with their friends. The sharing is a source of amusement for everyone. That's not a bad thing, but it sets up a competition between your social success and dating success which puts pressure on your dates to go bad. If you think you've become identified that way in your social circle, I'd suggest keeping your dating life private for a little while and finding other things to talk about with your friends. You don't have to completely keep them in the dark, but you can try being more terse in your updates.

Second, I would play with my expectations. Instead of trying to meet a guy, I would try to redirect my efforts into making friends. Sure, I would still be scanning and evaluating like the Terminator (can't really help that), but I would also make a conscious effort to get to know other people and give them a chance to get to know the real me. Shifting your focus like that has a bunch of advantages: it helps bring out the best in you by making you less judgmental and driven, which in turn brings out the best in others; it gives you a chance to meet friends of friends; it gives you a chance to get close to someone in a way you hadn't expected and maybe fall for them; it gives you a little break from the pressures of dating; and, it prepares you for the possibility of not meeting someone by building a strong social network underneath you. Neither of us can say for sure whether or not you'll meet a guy you'll want to marry, but shifting your focus will benefit you either way.

Third, I would start going on adventures that offered me lots of joy. I wouldn't hinge my happiness on whether I found someone to mate with. Sure, it'd be nice, but being single, having friends, (casual sex?) and lots of free time to dabble in different intellectual and spiritual disciplines is still a pretty sweet deal. I'd probably pick a project and devote a year to it. So far on my list, I have: compare the way people baton (express themselves with their hands), catalogue the purposes of conversation, live in a commune, open a cafe somewhere, and decode the secret language of crop circles (I shit you not). What's on your list?

To sum up, I don't think think people ever really miss the boat, and learning a lesson, even if that lesson comes late, is better than not learning the lesson at all and ending up divorced or in a empty marriage. But even if you do end up missing the love boat, there're still other boats in transit that can take you to the same destination. If you'd like to write back, feel free.