Anonymous asked: My tutor, female, seems like she might be interested in me, and I am interested in her. She's a student tutor and we are the same age roughly. We have 3 appointments left before the semester ends. How I could ask her out without making her uncomfortable? Should I be overt and just asks if she wants to hang out? Or ask her if she wants to help me prepare for my final in her free time (plausible deniability)? Or some other smart way? She is nerdy and shy, if that helps! I am a dude. Thanks!!

Ok definitely don’t ask her to help you study if you have other intentions. That’s deceptive. Don’t ever be deceptive. And, generally speaking, there’s no point in beating around the bush. But asking her out could make her uncomfortable and be destructive to the student/tutor relationship. I would wait until the last appointment, at the end of the appointment. When you’re done and she’s not going to have to be your tutor again in the future, thank her for all the help. Then say you like her and you want to see her again. Ask her if she’d like to go on a date, now that she’s no longer your tutor. Don’t be vague about what context you want to hang out in. Be direct. If she says no, it might be awkward for that last couple of minutes - but then it’s over. She doesn’t have to see you again, and vice versa. If she says yes, it’s great, you can go out, and since you don’t need her to tutor you anymore, the budding romantic entanglement won’t end up distracting from your study sessions.
Always be forthright, always be direct, and sometimes…be patient wait for the correct timing.