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Wayne and Wanda: Testing -- and treading -- the dating pool waters

  • Author:
  • Updated: April 29, 2016
  • Published July 31, 2014

It's so easy to meet people these days. Between social media, online dating, traditional blind dates, or au naturel meetings at the gym or the bar, finding someone to flirt and swap texts with is achievable, especially for those who work at it. But then comes that all-the-pressure-is-on first date, where you know whether there's a spark – and, potentially, a future. Readers have recently written in seeking help:

Dear Wayne and Wanda,

I want a boyfriend and I have been working hard to find one. I spend a few hours a day on just about any site you could think of – from Match to Tinder to eHarmony. I search as far north as Talkeetna and as far south as the Kenai. I've met up with lots of guys. But it never goes past the first date. I don't get it. I put a ton of thought and time into what I wear, where we go and what topics to cover. I think I convey tons of enthusiasm, yet they always end it with a polite hug and I never hear from them again. I'm cute, I'm employed, I'm not an ax murderer – what am I doing wrong?!


I appreciate your hard work and hustle. I firmly believe that you make your own breaks in life, and you are certainly doing everything in your power to accomplish the goal of landing a man and a mate. I'm also a firm believer in timing – and that's something you can't force, no matter how hard you work.

Right now, sadly, your timing is off. But, as the Great One, Wayne Gretzky, once said, you miss 100 percent of the shots you don't take. So keep shooting. Don't get frustrated and don't give up. Put your heart and your best self out there and eventually you're going to show up to one of these first dates and have your socks knocked off! Go get 'em!


It's one thing to hustle. It's another to come off as manic. Hours a day on dating websites and obsessive pre-date attention to detail? I can only guess how eager you seem up close and personal. Energy and sincerity are good qualities, but you may be coming on too strong. Enthusiasm, while terrific, can be misconstrued as desperation.

The next time you have a first date lined up, take a deep breath, relax, and tone it down. Let him do some of the steering, and enjoy the ride.


Dear Wayne and Wanda,

I'm kind of a shy guy. I've had a few relationships that were always with women I knew for a long time and had friendships with, and those friendships developed into something more. But I've been single for a while and have tried meeting someone online. I enjoy browsing the photos and reading about people's interests, but it never fails that when I've exchanged some emails with a girl and she suggests meeting, I freeze, I panic and I just stop replying. I can't get over the idea that meeting in person would just be so awkward. Of course I realize that if I'm not willing to do so, I'm wasting people's time. I really do want a girlfriend. How can I get over this fear of meeting in person?


I'll let you in on a secret: the women are just as scared as you. No one ever really gets over feeling a little weird about the inherent awkwardness of meeting a stranger. It doesn't matter whether you've exchanged texts and emails; there is something unknown about that first in-person meetup. On some level, we're always wondering, why are they still single? What's wrong with them?

We dread the loss of the fantasy when we take the relationship to the reality level. But guess what? No reality, no real relationship. So take baby steps. Schedule a short, informal, easily escapable date, like one drink, or one cup of coffee. No spark? Don't feel guilty. Do the gentlemanly thing, thank her for her time and wish her luck in her search.


Wanda played the good cop, so I'm giving our shy guy a little tough love. Buddy, you aren't going to get out of your dating rut without putting yourself out there. It's just the way it is. So spray on some Axe, brush your pearly whites, take a deep breath and go out! Yes, even force yourself to have a conversation and a few drinks with a complete stranger. The more you go out with women, the better the odds that you meet someone who clicks. And the more it will build your confidence and shake away your shyness, even if the dates don't exactly work out. Plus, the first step of getting comfortable with someone is getting to know them, so that starts with a first date.

I know it's easy to hang out -- and make out -- with people you're already familiar with. But these are clearly unfulfilling dead ends for you now. There are thousands of new, interesting women out there, just a click away. And believe it or not, a few are dying to meet a shy, awkward guy just like you. Really – some women are into that! So get out there!

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