Shouldn’t I have met someone by now?


Longtime reader/lurker here. I'm at a bit of a crossroads and I have no idea what to do.

I'm a 29-year-old guy living in Boston, and I've got a job that's turning into a career, an apartment I love, friends, and a bunch of hobbies that take up a lot of my time. I'm lucky that way.

A year and a half ago I got out of a long-term, live-in, toxic relationship that took up most of my 20s. My ex was emotionally abusive and cut me off from my friends and family, despite their efforts to help me. After she dumped me for the umpteenth time, I had the good sense to fend off her attempts to reconcile. It took some help from a therapist, but I finally rebuilt my life, got promoted at work, got my own place to live, and realized the things I needed to do better in relationships.

About six months after the breakup, I started casually dating a friend. We decided to take things very slowly, and eventually, over a period of months, we became exclusive and I developed really strong feelings. Shortly after, she pulled away and ended up dumping me a month later. She moved on to someone else immediately and we aren't really on speaking terms. I've been on a couple of dates since, many of which were terrible.

I've never believed in "the one" concept. I always thought that there are many good matches for a person. But I'm starting to believe that maybe no matter how badly I'd like someone good in my life, I'm just not supposed to have it. Shouldn't it have worked by now? Most of my friends are happily paired off, and I'm starting to get family pressure too.

My previous relationships have taught me that I'd rather be alone than settle for the wrong person, but I'm still lost at sea about how to deal with the loneliness that always sneaks up on me when I'm not expecting it, no matter how busy I keep myself. Or am I doing something wrong?

– Underwhelmed in Allston

All of this sounds OK to me. You were in a bad relationship for most of your 20s. Did you really think that at 28 or 29, someone would just hand you a soul mate so you could have this all figured out by 30?

Perhaps you assumed that this relationship with your friend would be the answer to your problems -- that you'd couple off with her and say, while smiling at the heavens, "It was all meant to be." But you said it best -- there is no "one." There are just people and experiences, and you need to keep having them. This negative stuff that you're feeling is just the aftermath of a disappointing and hurtful breakup.

It'd be helpful to spend time with your still-single friends. Not everyone is coupled at 29, and you need to keep some perspective. Also remember that loneliness hits all of us, even people in relationships. All you can do is keep dating and enjoying your great life.

Readers? Should it have worked by now for him? Did anyone feel this way at 29? Give him some context, please. Help.

– Meredith