The Hook Up: How to take a casual relationship to the next level

I’m in the midst of my Masters and I’m tutoring as a part of bursar work. Last year I worked with the first years, and I had my eye on a particular girl. She always acted a bit funny around me, but I chalked it up to shyness and thought she would never be interested in me. (Not a lot of self-confidence at that point in my life.) Then, at an end of year blow-out, she’d had quite a bit to drink and was like “I’m a lesbian!” But I still had to be a part of the exams, so I held back. I was a lot more closeted myself then.

Fast-forward to now, when my tutoring has me working with the second years for. And of course, this girl. I really like this girl. The problem is that she’s always surrounded by her friends. But then there are these moments, little smiles and awkward giggles. I’ve asked only her to be my friend on Facebook, and she accepted the same day! A friend of mine says I should ask her out for a coffee, but I’m scared I might scare her away! And what if we have nothing to say to one another? Worse, what if it’s all in my head? I’m so conflicted! What should I do? I’ve never really liked a girl like this before. It’s exhilarating and exhausting!—Smitten

Anna says: Scare her away from what, exactly? A Facebook friendship and a few awkward giggles? Assuming that there are no rules against tutor/student relationships that could get you fired, then yes, please ask her out for coffee. If you have nothing to say to each other, then you’ll only be out an hour and $1.95, no big loss. Or better yet, ask her to take a walk. Walking requires $0 and is less awkward than coffee because you’re moving and can comment on what’s going on around you. But ask her to do something. You owe it to yourself. And now you owe it to me and all of those reading. How’s that for motivation? Internet peer pressure!

If you want to wait until she’s no longer a pupil, then that’s fine, but don’t dawdle forever. Drop the doubt, ask her out. There, I made it rhyme for you. Every moment you spend tormenting yourself wondering “what if” is a moment you could be spending with your new girlfriend playing hide the epistemology of classification, or whatever it is people do in grad school.

If you need more suggestions, read this Hook Up column on how to overcome shyness.

Now go! Go, go, go. Seize the dame! Today is the first gay of the rest of your life, and all the other life-affirming slightly altered quotes! We’re rooting for you.

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your The Hook Up questions at

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