I Haven’t Had a Boyfriend in Five Years

Dear Meredith,

I'm female, straight, 32 years old, smart and attractive. I haven't had a boyfriend in five years, and I'm starting to consider it a serious problem.

Some factors that I think contributed to this problem:

- I've had boyfriends and dated, and they were perfectly nice, but flakey. Not guys I would consider a partner to build a future with. I pride myself on being the opposite -- if I say I'm going to do something, I do it. As a result, I admit I find it difficult to give new guys I meet the benefit of the doubt.

- There was a three-year period when I decided to make a career change, which also coincided with the breakup with my last boyfriend. As a result, I made a conscious decision to focus on my career, and my dating life vanished. Now I have more work-life balance, but after going so long without a partner, I know I can survive without one. But I don't want to. I'm scared I'm going to relegate myself to being an island forever.

- I'm shy and living in a new city, so meeting new people can be intimidating. I've tried online dating, but my heart's not in it. I go on a lot of first dates, but I'm rarely interested seeing anyone for a second time.

Do I need a therapist or just a kick in the pants?

– I'm a Rock and an Island


You just listed a bunch of reasons why you haven't had a boyfriend in five years. They all make sense, so there's no reason to worry. Therapy wouldn't have occurred to me. Just a light kick in the pants.

I'd only give you that light kick to get you to go on a few second dates. But only when you're on the fence after the first one. If you know you're not into someone after a first date, that's OK.

You might want to focus on building your community in this new city, because friends are just as important as boyfriends right now. Try some area activities and force yourself to mingle. Because a string of bad first dates is only tolerable if you have friends for balance.

Readers? Therapy? Kick?

– Meredith