Don’t wait for graduation: how to ask out your classroom cutie

I want to show him I’m interested, or ask him out, but I’m worried that if he’s not into it or things go south, it’ll make things incredibly awkward in class.



By Yours Truly (The Cascade) – Email

Print Edition: January 28, 2015

There’s this guy in my history class that I’m really hitting it off with. At least I think so. We’ve been assigned the same discussion group. I want to show him I’m interested, or ask him out, but I’m worried that if he’s not into it or things go south, it’ll make things incredibly awkward in class. Please advise!

—Awkward Historian

Dear Awkward Historian,

It becomes difficult in situations like this to discern whether someone is genuinely interested in you or is just trying to be polite. This guy is obligated to talk to you, and whether he genuinely likes you or not is for him to know and for you to find out. The difficult part is doing so without making you want to skip out on the rest of the semester’s history class.

According to self-described dating expert, romance coach, and blogger Evan Marc Katz, a woman should never ask a guy straight-up if he wants to go out with her — rather, she should use her “feminine wiles” to get him to ask her out. He suggests a man might be scared off by a woman being too “masculine.” I call sexist bullshit. Since when is being assertive a masculine quality? If you know what you want, go get it in a considerate manner.

First off, be light in your approach. Don’t flirt heavily, or ask him off the bat for the whole dinner-and-movie thing. Start with asking him if he wants to join you for coffee during the break. Make sure the rest of your discussion group is out of earshot, unless you want a Timmys entourage. If you haven’t already, try steering the conversation away from history. What are his likes, his dislikes, his passions, and life goals? View this as an opportunity to screen him as a potential boyfriend. Outside of class, how aligned are your interests?

If things keep progressing, try asking him to have lunch before class — something on-campus and convenient. If he’s up for that, and you’re still getting along well, take the plunge. Be candid and straightforward. Do it while walking or finishing up coffee; this way you’re not trapped with him for another half-hour while finishing lunch or, worse, about to sit through a whole class together.  Remember that being asked out, when done tactfully, is only ever a compliment, even if the askee isn’t interested.

If things do go south, continue being friendly and keep up your conversations. As difficult as it might be at first, it’ll significantly lessen any awkwardness for you.

You might want to question whether you want to pursue this as a romantic relationship. If you’re not itching to jump into bed with him, why not consider this as an opportunity to gain an opposite sex confidant and genuine friend? Your call.

I wish you good luck, and I hope you get married and name all your children and pets after esoteric historical figures!

Next week with Yours Truly:

My partner views a lot of porn and it makes me uncomfortable. He doesn’t try to hide it from me, and it’s not hardcore or anything, so should I be weirded out by it? I read that it’s normal. Should I be concerned?

—Porn Doesn’t Please

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