Wanderer Online Sex Advice: Initiating the Date | By Gina Wicentowich

Every week, Darren Tardif brings you the male perspective for relationship and sex advice, dishing on first dates, prostates, and other relevant stuff. Today, we’re excited to add Gina Wicentowich to the mix. Feel free to send either Darren or Gina your questions at thewanderersex@gmail.com.


There’s this boy I really like… and we’ve been talking over Facebook but I’m not sure what to do at this point. He’s not making a move. Should I make a move and ask him to hang out? Is it bad when girls have to ask a guy to hang out because the guy should do the asking?

-Scared to initiate THE DATE

First off I would like to do a little rant about the olden days. Back in a world of 60’s housewives and Don Draper look-alikes in black suits… before the invention of the iPhone 5 or tweeting, boys liked asking girls on dates. I find this phenomenon has died out. Girls now have to take the lead. It’s not quite a generalization but just the reality from my 21 years of experience. Don’t take any offense boys, just give us a little bit more love and we’ll be more receptive when you ask. Boys would be surprised. When I’m out on Whyte, if a boy just comes up to me and asks “How’s your night” I will swoon. Want to know why? It doesn’t happen. Instead I get the “Hey maaa, I’d like to cook you breakfast in the morning” or (insert corny line here).

Sadly, there is no dating-for-dummies. There is no perfect solution to win a guy over. Every guy is completely different, although all smart enough to not ignore pretty girls. If he is consistently responding to your messages on Facebook then that is a good sign! If he’s taking the time to find out what’s going on in your life then there’s a good chance he’s interested in you.  Why else would he listen to all the specifics about your classes? But there is nothing wrong with a girl asking a guy to hang out. Let’s be real. And I’m not going to pull any this-is-the-twentyfirst-century-women-have-equal-rights crap. 95% of guys need a good push into the dating world – they need a hint to let them know you are into it. Sometimes it’s a very direct, bold hint. So just ask him to hang out. Be chill, casual, and vague. Use the words “hang out” opposed to “formal dinner at The Keg where you need to wear a tie.” It’s as simple as, “what are you up to this weekend? Let’s hang out.”

From there it should be a natural progression. You guys should do something fun and interesting. And since he knows you’re game he should be able to take control of the wheel. If he doesn’t continue talking to you after the date, or doesn’t ask to endeavor on a second date, well, he’s not interested. The beginning should be the easy part. I know we’re all scared of rejection here but c’mon girls, Facebook makes things too easy for boys. They don’t even have to ask for our number anymore because they can somehow creepily find us and our phone number online. There is no harm in asking boys to hang out. In reality, we run this game. YOLO.

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