Dear Anon-O-Box: I’m Back On The Market

Dear Anon-O-Box,

I’m a guy – straight, a bit under 30. I’ve been off the market for awhile, but now that I’m back out there on my own….where do I start? My last two relationships came out of an introduction by a mutual friend in one case, and a chance meeting in another. I’m just not quite sure where to take things as I start from scratch.

- Back On The Market

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e answers:

Dear BOTM,

Assuming you haven’t moved, you aren’t starting totally from scratch. You still have a social circle, which connects you to a vast network of people and potential new girlfriends. My male clients are always wary about my advice to go out and get more guy friends until I explain that for every guy friend you have, you’re opening up your social circle to all the ladies he’s connected to in his social circle. Who knows, you may end up being the perfect guy for his girlfriend’s best friend’s sister!

Beyond your normal circle of friends, take stock of the activities you do outside of work. Do you have a gaming group? A volunteer group? A band? A coffee meetup where you all practice your French or German? Dance lessons? Keep your eyes peeled for potential singles wherever you go and don’t be afraid to flirt a little or do some stealth research to find out if that cutie you like is single.

FlipMe is a neat way to flirt with people you encounter out on your daily business. You register and get a small pack of cards, which you can then hand out to people who interest you. See someone at the bookstore who is checking out the poetry? Slip her a card. There’s a girl behind the counter at the coffee shop who is just adorable? Slip her a card. Each card has a flirty message and a URL and special code on the back. When the girl gets home, she puts in the code and can see a picture of you and a (very) short profile. She can then decide to email you through the site (or not). It’s a very neat and low pressure way to say you’re interested.

And of course, there’s online dating. From the sound of your email, you haven’t gone that route yet, and if you continue to be lucky with the folks you know out in your daily life, you may not need to. But if you feel like you’ve exhausted your connections and don’t have the time to add another activity to your social life, online dating is a great way to access a pool of singles you may not normally run into out in the world.

My advice for newbies to online dating is to sign up for two sites – one paid, one free. I generally recommend Match for the paid site since it’s the industry leader. They’re not perfect (no site is), but they’ve been doing it right for years and have a large community of singles. If you’re Jewish or Christian and interested in a faith-based match, make JDate or ChristianCafe your paid site. For a free site, OkCupid is my recommendation. Lots of geeky folks there!