My best friend’s a tool when it comes to women, and I really don’t get it. We’re both decent-looking guys with good jobs and lots of confidence. To top it off, he’s probably seen every pick-up video out there, but when it comes to talking to women, he can’t close the deal. He tells me to hold him accountable when it comes to getting numbers, and when we’re on the way to a club he’ll keep talking about how psyched he is and how he’ll do this or that, but once we get there, he just stands around and getting him to approach a woman is almost impossible. Any suggestions?

Andrea: Dear BFF,

It sounds like you’re a pretty good wingman. Although holding him accountable, monitoring him, and pushing him can be helpful at first, continuously doing so will take away your effectiveness as a motivator.

Think about it: he keeps “failing” despite your pushing, and nothing happens.

 

Why should he change?

Try a different tactic: before going out, have him take out $50 from his bank account and give it to you to hold on to (increase the amount if he’s wealthy). If he gets a number that night, he gets it back. He does not get it back (don’t spend it) until he gets a number. Call it a “date trust fund.” Paying him will be a positive association with getting girls’ numbers and inaction will cost him. Let me know how it goes!

Claire: Dear Wingman,

There is a funny phenomenon that says we often react in contrast to those around us — in other words, your confidence might actually bring out his lack of confidence. I’m not saying that’s the cause of his un-Romeo-ness, but maybe it’s time for another approach. Maybe he should try dating online — it will give him more control over the situation. He can keep things light for as long as he likes, and use online chatting and emails to get to know the woman he eventually chooses to meet.

It will allow him to build his confidence, which seems to be lacking. Good luck!

• Two sisters, 20-something Andrea and 30-something Claire, offer their differing views on your relationship issues.

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