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Hi Yana,

Where is the line between “If you like someone, ask them out!” and “Oh, that guy asks everyone out”???

— Master Dater

From your question, it sounds like you like a lot of people. Maybe you’re getting some flack for that from friends or foes? True, you don’t want to make your potential dates feel somehow unspecial because they saw you on campus asking out everyone else around you — and left them as the 24th person you’ve asked out in a day. Then again, if you like someone and want to go on a date with them, you should ask them out!

So, where’s the line? I’d draw my line around the borders of “Am I asking everyone out for genuine reasons?” and “Am I attempting to fill a void or accomplish something that has nothing to do with the human I’m asking out?” Meaning, are you on an asking-out rampage because you genuinely want to go out with these individuals? Or are you trying to put a finger in your emotional dam and any old finger will do?

Of course, you can finger as many emotional dams as you want. You know me, as long as everyone going out with each other is consenting to your dynamics and what y’all are doing together, then there’s nothing wrong with going out with a bunch of people just for fun. Not every date, hook-up, or relationship has to be goal-oriented and meaningful. But your dates should know if that’s your outlook.

As far as what everyone else thinks about your dating habits, you can never achieve 100-percent approval when it comes to sex and dating. As long as you keep your creep-factor low (like maybe don’t ask someone out, get rejected, turn to their best friend standing next to y’all, and ask her out) and respect the people you’re asking out for the unique reasons you like them as individual people, then you can forget the haters and get on with the daters!

***

Hi Yana,

I want to be able to have a polyamorous relationship. How do I find people who want to have the same thing?

— Pursuing Poly…click here to read the response…