Starting now, take responsibility for your feelings and decisions
Q: I am a 38-year-old never-married man. My friend is a 27-year-old never-married woman. I've had a crush on her since we met nearly three years ago but never asked her out because I thought the age difference would be too much for her.
Well, for the past eight or nine months she has been dating a guy my age who has lied to her and cheated on her. He has been divorced twice and has kids from at least one of the marriages.
I want to talk with her and persuade her to break up with him, but even though that would be my advice if I didn't have a crush on her, since I am crazy about her I'm worried that my motives aren't the best.
And my feelings for her aside, should I ever say anything to her, under any circumstances, about what a bonehead she is for dating this guy?
And while I'm at it, can I go ahead and throw out the obligatory woe-is-me, why-do-nice-guys-always-finish-last question?
Frustrated in Florida
A: She may be a bonehead for dating this guy, but you're a bonehead, too, for:
1. Not asking her out.
2. Giving a silly reason for not asking her out, since "I thought the age difference would be too much for her" means you're either blaming age instead of admitting you were too chicken to ask her out, or making decisions based on what you presume she wants without even checking with her.
3. Taking her relationship with the older guy as evidence that she screwed up by choosing him, instead of evidence that you screwed up by not asking her out three years ago.
4. Judging the guy for being divorced with kids. It's the how and why that matter, not the what.
5. Thinking it's your place to "persuade her to break up with him."
6. Hoisting the banner of misunderstood nice guys, when you're not a spokesman for any interest group here, you're just a guy who chose not to act on his feelings and now wants to blame everyone but himself for the fact that the girl is with someone else.
When it comes to taking responsibility for your own feelings and decisions, "immediately" is the best time to start.
Tell your friend you've had feelings for her for a long time, and you held back for reasons that now seem stupid in retrospect, and if she were with someone who was treating her well, you would shut up and wish her the best. But since this guy isn't treating her well, you're disclosing your bias up front so you can say out loud that you think she's wasting herself on this guy. And that you hope she'll recognize this and choose someone who does value her — even if it's not you, though you would clearly prefer that it is.
Even if this turns the entire situation your way (and the sky rains rose petals and angels sing), please also take a hard look at other parts of your life, to see whether blaming rivals/bystanders/the cosmos for failing you is a tactic you've relied on before when things haven't gone your way. It's a very common, very tempting habit, as well as one best kicked for good.