Five years ago, when I was 23, this guy had a crush on me. I was kind of attracted to him, but his crush was so obvious it made me uncomfortable. Also, he had the worst hair and clothes — shiny polyester op-art print shirts and Cosby sweaters. I ended up blowing off dates with him twice, and, unfortunately, my roommate told him to back off in an extremely cruel way. Since then, I\’ve run into him periodically, and he\’s always friendly. I\’ve come to realize he\’s one of the kindest people I know, plus he\’s smart and has the deadpan humor I prize. Also, he\’s suddenly well-dressed and looks hot. It just hit me: I totally want him. I e-mailed and asked if he wanted to hang out sometime. He never answered. I feel sad, guilty and confused. Do I not deserve his friendship after the jerky way I treated him?

— My Bad

Five years ago, you were probably smack in the middle of that charming stage common to people in their early 20s, \”If you like me, you\’re obviously a steaming pile of poo.\” If this guy hadn\’t made himself so easy to despise, with his disco dirty-old-man shirts and his tendency to spell out your name in drool, you would\’ve found some other reason, like the fact that he has ears.

All you had to do was tell him you weren\’t ready for a relationship. Why did you instead say yes to dates and no to actually showing up for them? Maybe because you bought into the prevailing notion of the relationship as a voucher for happily ever after, making it hard to entertain the idea that there could ever be a bad time to leap into one. In your defense, one\’s 20s are not generally known as the decade of great genius. Per a sympathetic letter I was inspired to write Monica Lewinsky in 2002: \”I did some completely dumb things in my 20s — everybody did. The only thing that makes you different from the rest of us who fucked up as 20-somethings is that our mistakes didn\’t get splashed across the international press.\”

Times have changed. You\’re almost in your 30s, people are having Cosby sweater parties, and Monica just graduated from the London School of Economics. Still, if the guy was drooling for you then, he probably has at least a little corner-of-the-mouth dribble for you now. So, why no response to your e-mail? Maybe it got snagged in his spam filter with all the HOT TEEN SLUTS! — or maybe he got your e-mail, and in the cold light of history, translated \”Wanna hang out sometime?\” as \”Wanna get hung out sometime?\”

Instead of sitting around feeling sorry for yourself, get on the phone and say you\’re sorry to him: I was a jerk, I’m less of a jerk now, how ’bout you let me prove it to you over a drink? For future reference, any guy (no matter how mouthbreathing or short on teeth) who lays himself on the line asking you out deserves a little kindness in return. This doesn\’t mean leading him to believe he has a chance. Determine your threshold for, say, petroleum-based fashion and a nerdfro, then be straightforward without being too straightforward, i.e., merely let him know that dating you is a no-go. No need to get into your ban on being seen with men in sweaters illustrated with radioactive centipede porn.

Toad rage

I decided to \”lower the bar\” for this short, chubby guy with a nose ring because I was attracted to how self-possessed and quietly confident he seemed. I arrogantly thought he\’d be really excited, but he totally blew me off. After we made out at a party, he waited a month to call! Somewhat hesitantly, I agreed to a date — which he canceled via voicemail! How do you get repeatedly rejected by a toady guy and still feel good about yourself?

— Reeling

There\’s a certain kind of man — for example, short, chubby, and nose-ringed — who should be grateful you even spoke to him at a party and didn\’t just set a cocktail napkin on his head so you\’d have a place to rest your drink. Of course, it helps if he understands that\’s the certain kind of man he\’s supposed to be. Pay attention when a guy has quiet hotitude. Confidence reflects value. As for your confidence in your own value, even if a two blows you off, that doesn\’t mean you go from a 10 to a 10 divided by two. Who knows, maybe this guy\’s a player, or on the rebound, or maybe you\’re just not his type. Then again, maybe you might have been his type — had you turned on the charm you would\’ve if he\’d been shaped more like a soccer star than the soccer ball.