Help Desk

:( Help!

I've lost a lot of hair in the past few years. Now I'm single again and getting on OkCupid. What are the rules for keeping an online photo up-to-date, and how much can I bend those rules?

– Photos Always Tell Everything

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The simple answer to this question hasn't changed in the past decade, PATE. Your online dating photos need to give people a realistic idea of what you look like now, for their sake and for yours. If your dates are jonesing for a full, luscious head of hair, you're not gonna want to deal with the disappointed looks and glances to the exit when they encounter your shiny dome. Honesty will help you avoid wasting your time.

We're not saying that you can't use older photos as part of your dating profile. As dating sites increasingly eschew text in favor of images, the role of pictures in these self-advertisements has changed. Most profiles now contain a mix of images, each serving a unique purpose: the Me-on-My-Best-Day photo, the Proof-I-Have-a-Sense-of-Humor photo, the Aren't-I-Quirky-Because-I-Once-Wore-a-Fake-Mustache photo, the Exotic-Locale photo, the Conversation-Starter photo, the Disclosure-of-Physical-Flaw-Not-Apparent-in-My-Me-on-My-Best-Day-Photo photo, etc.

It's on you to own up to your baldness, PATE, but don't feel obliged to dwell on it. If you have an older photo that's notable for some other reason (exotic locale, fake mustache, conversation-starting hobby), you should still feel free to feature it. Just get around to addressing the situation upstairs in one of the subsequent images. (Or, if you're "that guy," just crop the tops of your photos or wear a hat in all of them. Your future dates will know exactly what's up.)

There are many fish in the sea, and plenty of men and women out there who can't resist the Daddy Warbucks look – or even the George Costanza look. We recommend that you wear it with confidence and that you focus on pursuing romantic prospects who are legitimately interested in dating someone your age. Don't corner yourself into pretending to be someone you're not for the sake of attracting someone who wouldn't be interested in the real you. It's a losing proposition.

In general, try embracing the fact that you have some miles on you. Let potential dates know what you have to offer – the wisdom and experience of the past few years you spent in a relationship, for one. What else? An adult sense of responsibility? A career that's advanced beyond "aspiring drummer"? The ability to relate to the millions of other people your age also looking for a connection online?

That said, it's up to you. If you prefer to chase after lost youth, there is actually an app out there for overcoming baldness. TrackMyHair, available for iOS, creates photo sets to monitor hair loss over days, weeks, and months, indexable against a calendar that tracks your adherence to various baldness-preventing medicines. Many have fought and few have won, PATE, but we're rooting for you. And if all else fails, you can always take the low-tech cure: a razor, some shaving cream, and pride in being a smooth-operating bald guy.

:) HD