I suppose in order to get genuine and beneficial advice I have to be brutally honest with myself. So, despite how difficult that can be, here it goes.
I am a single, never married man, rapidly approaching my 32nd birthday. The last half a decade has been both brutal and enlightening. I have gone from being an extremely successful financial professional in my 20s, to a struggling, in transition, professional in my 30s. After years of international travel, complete independence, and immeasurable experience, I am now between careers, living back at home, and digging my way out of bankruptcy.
Perhaps most troubling is that even when I was "on top of the world," I couldn't find the right woman. I have met and dated some beautiful, kind, and decent women. However, the biggest trouble is that I am an introvert and that I do not agree with the consumption of alcohol. In my opinion, the affects of alcohol are like any other drug, and they give irresponsible people a "get out of jail free card" for their often reckless behavior. I have found that most unmarried women in their 20s and 30s prefer bars, clubs, and concerts. I am a man who prefers museums, exercise, the opera, and quiet restaurants. I am who I am.
Whether it be online dating, common friends, or random acts of introduction, nothing has worked for me. So, my question is this: once I get my financial and professional life back in order (which may take years), which avenues to meeting women could I pursue that perhaps I have overlooked or previously disregarded?
– Sober, Bankrupt, and Befuddled, New Hampshire
I'm not answering this letter because I know of a magic place where you can find the right woman. I don't. (Although, I'm pretty sure that the Boston Symphony Orchestra has "Under 40" specials, as do many of the other classed-up artistic groups in town -- like this one.)
I'm answering this letter, SBB, because we need to chat about your self-esteem -- and your reality. I get that you're poor and living like a college kid, but you can't put off meeting people until you're comfortable with your place in life. You can't say, "I won't be ready for years!"
We're all works in progress. Some of us want to lose a few pounds, but when we finally do, we're out of a job. When we finally get jobs, we notice our receding hair lines. Rarely are we awesome in every way, all at once.
My advice is to make a list of everything you offer right now -- humility, the ability to be thoughtful, good taste … the list should keep going. You're not the only one who's not on top of the world right now. Don't take yourself out of the running. Go out, hang in the library, and sit in coffee shops. If you see a woman you like, approach.
And try to keep an open mind. I won't argue with you about alcohol -- you're entitled to your own set of beliefs and priorities -- but try not to be too severe about how you present your opinions, especially when you first meet someone. Just a tip.
Readers? Is he allowed to take himself out of the running? Am I wrong to say that he should put himself out there when he's not happy with himself? Thoughts on sober dating? Know how he can meet the right women? Tips? Discuss.