How about we…walk the High Line from north to south, then go get frozen yogurt?

How about we…check out the new exhibit at the MoMa then grab dinner/drinks?

How about we…find an intimate spot to aggressively thumb wrestle?

Wait, what?

How about we…work on your online dating profile a little bit?

Which is exactly what I did one recent Sunday when my best friend, ready to get back in the dating game, came over. Armed with the most flattering photos and the wittiest responses, we signed her up on HowAboutWe. The premise is cute and catchy: people propose dates in the form of a question—like the ones above—beginning with the phrase “How about we…”

But based on what we saw, it seems some of you might need some help.


How about we…use enticing photos that sell who you are?

Your pictures should say, “Hey cute girl, look at me. I’m cute too. We would have fun together.”

It shouldn’t say, “Oh, you again. You know what I like? Beer. You know what else I like? Sticking my tongue down my dog’s throat.”

Your main photo should be one of you smiling. You don’t have to be tossing your head back in laughter, but please look pleasant.

The other photos should show you doing your thing, whatever that may be. Action shots will catch a lady’s attention—surfing, skiing, riding a bike. Whatever it is you do, show us. Women love a man with active interests and hobbies. And we want to see you in your element. If that happens to be sitting in granny’s rocker on the porch with a beer in your hand, great—show me.

Just remember, as cute as you think you look on granny’s rocker, every picture sends a message. While I’m sure a lot of people on these sites are just trying to get laid, if you are serious about looking for someone to date, then put in a little effort. A lazy profile equals a lazy man. A lazy man is a lonely man.

If you have a pet, show them off too! But just one picture does the trick. How about we leave out the one where you and Fido look ready to play doctor? Instead, choose the one that best showcases your cuteness together and leave the rest on your iPhone to show off during the first date.

How about we…don’t use your work head shot?

Again, this sends the wrong message. While you’re all “I look professional and well-groomed in that killer suit from Barneys,” a woman is all “sorry Gordon Gecko, but do you ever get out?” While it’s comforting that you’re career-driven, putting your job title in your bio will do the trick.

How about we…use both a face and body shot?

Would you buy a house based on a blurry shot of the garage? No, because the owner is obviously trying to hide something—which is exactly what I thought clicking through profiles that day with my friend. So be honest with yourself and own what you look like—you won’t be able to fool anyone when you show up to the first date.

How about we…don’t show all our cards here?

On the first date, would you tell a woman that you have trust issues, a fear of flying, or a freaky fetish? Then don’t do it here either. I’d also leave out your views on politics, religion, and having children, unless these are non-negotiables for you.

Like that teeny spoonful you’re handed when you sample a flavor of frozen yogurt, online dating profiles are meant to give you a taste of the person. You want to show and tell just enough to get a woman’s attention. Draw her in with your wit (and honest pictures) then seal the deal in person.

How about we…be honest and funny?

This particular site has optional questions for you to answer, including what you’d like to come home to, and describe yourself in five sentences. This is your chance to make her laugh, so only dive in if you have an interesting or humorous reply.

You better tell the truth too, especially when it comes to exercise, drinking, and smoking habits. If you smoke, say you smoke. You won’t be able to hide it very long. And if you want to be someone who answers that you don’t smoke, then don’t smoke!


No one said this whole dating thing would be easy, but like I told my friend that Sunday when she came over, it’s a numbers game. The more you put yourself out there, the better your chances of meeting someone you like. So what do you say? How about we…edit your profile and see if this helps you score any hot dates?

In two weeks: Jamie looks back on a year of Getting Around Town