Miss Information

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Have a question? Email Letters may be edited for length, content and clarity.

Dear Miss Information,
    I’m a guy in his late thirties who happens to look much younger. I like to date women in their twenties; it just feels like a more natural fit. But as I test the waters of online dating, I’m finding that women immediately dismiss me as being too old, regardless of my photo. I don’t want to have to start lying about my age, but these first pangs of ageism are really bringing me down. Is there a better way to handle this whole age issue? — Dorian Gray


Dear Dorian,
    You can knock five years off your age in order to show up in more searches, provided you include a line at the end of your profile coming clean about your actual age and why your youthful vibe and appearance will refute the information on your driver’s license. The more preferable, less slimy option is to leave your age as is but make your profile more appealing to the younger set. A few tips on doing that:
    · Get highly specific about what you like — books, music, movies, etc. If a woman manages to find someone who shares her interest in late-’70s modern dance, it’s likely she’s not going to give a shit if he’s got a few gray hairs.
    · Eliminate any negative sells. Saying stuff like, "I’m more mature than those youngsters you date and have way more money too," only makes you look bitter and defensive. You have your own thing going, no need to put people down.
    · Get better photos and more of them. Stay away from black-and-white headshots and any pictures where you’re shirtless or standing next to a recreational vehicle. I cannot tell you how many older men I’ve seen make this mistake.
    · Even if you have no interest in dating women your age, don’t indicate that on your profile. Why? Because it makes you look like someone who’s only out to screw younger chicks. It also discourages awesome older women who may be a good match. Believe it or not, there are women your own age who look and feel just as you do. If you quit being such a hypocrite — complaining about age discrimination while you discriminate yourself — you might find them.

Dear Miss Information,
    I’m a woman in my mid-twenties who’s madly in love with a man fifteen years my senior. We dated for a year, but when the time came to decide whether we were going to get serious or move on, I freaked out because I was afraid of spending my golden years watching him deteriorate. We broke it off. In retrospect, I think I’m gun-shy because not long before we started dating, I ended a five-year relationship with someone who ultimately went batshit insane.
    That was three months ago, and I’ve regretted it ever since. We’ve remained good friends, and about a month ago, we started sleeping together again. I’m in therapy, but it hasn’t helped me make decisions. My friends say go back. My stepmother says go back. But none of them can tell me what I should do about his inevitable decline. Should I reconcile with him? How can I get over this crushing fear of growing old alone? — Neurotic

Dear Neurotic,
    If you’re waiting for a cure for old age before you settle into a relationship, prepare to be single for a long, long time. Just because he’s fifteen years older doesn’t mean he’s going bite the dust anytime sooner. You could marry someone twenty years younger who dies in a car accident and leaves you dateless on bingo night just as easy.
    Neurotic, I’m not totally convinced you want to get back together with this guy. I think you’ve analyzed the ever-living shit out of this and have come up with the he’s-gonna-die-on-me thing as your excuse for not making a commitment. This protects you from having to break up with Mr. Oldster, who’s been a source of comfort and security to you after your crazy shitty relationship with Mr. Five Year. I don’t blame you for doing that, but it’s also a pretty bad reason to commit to someone.
    Get back together with him, but give yourself a set time period — say, three months — after which you’ll end things if you’re still feeling uncertain.


Dear Miss Information,
    I just moved into a new apartment building, and there’s a gorgeous girl who lives down the hall. She gives absolutely the best head, waits on me hand and foot and expects no reciprocation. Thing is, I really don’t care about her, but she’s too convenient to turn down. How can I get myself out of this one without making life hell? I’m still going to have to be her neighbor. — Guy Next Door

Dear Guy Next Door,
    I’m going to save the old lecture about not shitting where you eat for another time. You’re in a real mess. Any woman who doles out blowjobs to near strangers and expects zero in return is likely to have some pretty serious emotional problems. Either that, or she’s just a sexually liberated chick who happens to find that kind of thing enjoyable, in which case you’re an idiot for questioning it. But I doubt it.
    Pick a time outside your normal hookup schedule (i.e., if you always come over at night, do it during the day) and pay her a visit. Tell her your casual sex days are over and that you’re seeing someone who lives in another town. Yeah, it’s a lie, but if she’s the persistent type, it’s going to be more of a deterrent than a simple, "I don’t want to screw you anymore." It’s also much easier to explain why a long-distance girl is absentee than some imaginary lady who lives nearby.
    Going forward, make sure to set the right expectations before you get intimate and remember that taking advantage of a sketchy situation, no matter how convenient, is never cool.

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