Dear Carolyn • 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 last 8 or 9 months she has been dating a guy my age who has lied to her and cheated on her. 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

Dear Frustrated • 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) 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. 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'd shut up and wish her the best. But since this guy isn't treating her well, you're disclosing your bias upfront so you can say out loud that you believe 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'd clearly prefer that it is.

Carolyn Hax's column runs Mondays, Wednesdays and Fridays.