When to ask someone out?
June 1, 2015 4:47 PM Subscribe
I totally want to ask someone on a date. I think there's mutual chemistry.. maybe. Complications: I'm her (paid) tutor. But then again, she's older than me, and we're both in our late 20s/early 30s.
I met Sandra and Sean through a friend (John). They were both looking for tutors - long story short, I started to tutor Sandra and Sean in a subject that I know well - let's say it's programming. They're paying me very very fairly, and I'm actually very happy to teach the software, because it helps hone my own teaching process (I partially teach for a living).
Sean is great. Sandra, however, is really awesome. She's really interesting, thoughtful and compassionate, has a great laugh, really lovely, but also is super put-together, super intelligent, full of calm determination, independent, and successful in her own pursuits. We have really interesting conversations together (albeit with other people, in a group). I can't tell if she's interested in me or not, but she has mentioned that she's single, is touchy-friendly, and she's always happy to suggest to activities that the four of us (including John) should do together. (John is happy in another relationship, and assume that Sean is completely uninterested.)
I'm totally crushing on her in a way I haven't in years - in like a 'hey, this could be a Really Meaningful Thing' kind of a way. At the same time, it's only been about two weeks since I've met her. I'm also her and Sean's tutor, after all. The tutoring isn't for a school or a for-credit class, and there are no grades or anything, so I'm not too worried about a conflict of interest. She's in her early 30s, while I'm in my late 20s, and I'm a cisgender male.
Part of me says - 'C'mon, ask her out on a date while you have chemistry!' The other part of me says - 'Wait, you're talking and hanging out for four weeks anyways, so have fun just hanging out, and ask her out then after tutoring ends. Why rush things?'
What say you, AskMe? Do you think that the tutor dynamic is strange / weird? Should I bit the bullet and ask her out on a date now? Or should I let the month pass by, and then after our tutor/tutee relationship is over, ask her out then?
I met Sandra and Sean through a friend (John). They were both looking for tutors - long story short, I started to tutor Sandra and Sean in a subject that I know well - let's say it's programming. They're paying me very very fairly, and I'm actually very happy to teach the software, because it helps hone my own teaching process (I partially teach for a living).
Sean is great. Sandra, however, is really awesome. She's really interesting, thoughtful and compassionate, has a great laugh, really lovely, but also is super put-together, super intelligent, full of calm determination, independent, and successful in her own pursuits. We have really interesting conversations together (albeit with other people, in a group). I can't tell if she's interested in me or not, but she has mentioned that she's single, is touchy-friendly, and she's always happy to suggest to activities that the four of us (including John) should do together. (John is happy in another relationship, and assume that Sean is completely uninterested.)
I'm totally crushing on her in a way I haven't in years - in like a 'hey, this could be a Really Meaningful Thing' kind of a way. At the same time, it's only been about two weeks since I've met her. I'm also her and Sean's tutor, after all. The tutoring isn't for a school or a for-credit class, and there are no grades or anything, so I'm not too worried about a conflict of interest. She's in her early 30s, while I'm in my late 20s, and I'm a cisgender male.
Part of me says - 'C'mon, ask her out on a date while you have chemistry!' The other part of me says - 'Wait, you're talking and hanging out for four weeks anyways, so have fun just hanging out, and ask her out then after tutoring ends. Why rush things?'
What say you, AskMe? Do you think that the tutor dynamic is strange / weird? Should I bit the bullet and ask her out on a date now? Or should I let the month pass by, and then after our tutor/tutee relationship is over, ask her out then?
You have a month-long tutoring arrangement, and not an indefinite thing? Please, please wait. Ask her out only after the professional relationship is over.
posted by brainmouse at 4:49 PM on June 1, 2015 [16 favorites]
posted by brainmouse at 4:49 PM on June 1, 2015 [16 favorites]
I'd recommend waiting until the month is up + an extra week or so before asking her out.
posted by kinddieserzeit at 4:51 PM on June 1, 2015 [9 favorites]
posted by kinddieserzeit at 4:51 PM on June 1, 2015 [9 favorites]
It is super mega inappropriate to ask her out while you work for her.
posted by Jairus at 5:08 PM on June 1, 2015 [10 favorites]
posted by Jairus at 5:08 PM on June 1, 2015 [10 favorites]
Wait. If only because it's unfair to Sean otherwise.
posted by jaguar at 5:08 PM on June 1, 2015 [6 favorites]
posted by jaguar at 5:08 PM on June 1, 2015 [6 favorites]
For whatever it's worth, it wouldn't bother me if I were her/your tutee in this kind of informal situation, but on the off chance that she's more like wintersweet above, definitely hold off a few weeks to give yourself the best shot at success!
posted by treehorn+bunny at 5:09 PM on June 1, 2015 [2 favorites]
posted by treehorn+bunny at 5:09 PM on June 1, 2015 [2 favorites]
Chill. Wait. Continue to be fun and flirty while also professional.
she's always happy to suggest to activities that the four of us (including John) should do together.
And keep going on these outings.
posted by OnTheLastCastle at 5:12 PM on June 1, 2015 [4 favorites]
she's always happy to suggest to activities that the four of us (including John) should do together.
And keep going on these outings.
posted by OnTheLastCastle at 5:12 PM on June 1, 2015 [4 favorites]
(That is, it's unfair to Sean if you're tutoring the two of them together. If you're tutoring them separately, I'd still wait.)
posted by jaguar at 5:14 PM on June 1, 2015
posted by jaguar at 5:14 PM on June 1, 2015
Given the short period of time, I'd wait, but not so much because it's super-creepy as because there's a possibility that the rest of it'll be uncomfortable if she's not interested, even though I don't think this feels predatory. But a big part of it is also that clearly you're a bit nervous about this, which is natural, and you're coming up in a very short period of time on a much more natural segue into this. "This has been so fantastic. I really like spending time with you. I was thinking, since we're not going to have this tutoring time now... do you want to go have dinner sometime?"
It's not like summer camp where at the end you're going to go home and not see her again until next summer. No need to rush into it.
posted by Sequence at 5:35 PM on June 1, 2015 [10 favorites]
It's not like summer camp where at the end you're going to go home and not see her again until next summer. No need to rush into it.
posted by Sequence at 5:35 PM on June 1, 2015 [10 favorites]
If she says no but you have to keep tutoring her that is going to be awkward af. Wait it out and get in touch a few days after.
posted by turbid dahlia at 5:55 PM on June 1, 2015 [1 favorite]
posted by turbid dahlia at 5:55 PM on June 1, 2015 [1 favorite]
Keep tutoring her, keep going out to things she suggests and reciprocating whatever flirty signals she sends your way, and ask her out on a date when the tutoring is over. Good luck!
posted by lafemma at 5:57 PM on June 1, 2015
posted by lafemma at 5:57 PM on June 1, 2015
I really think she may ask you out when the tutoring sessions are over. If not, I think it'd be perfectly legit for you to ask her. It definitely sounds like she likes you a lot: it may be as a friend or it may be as a possible romantic partner.
I don't think it would be morally wrong to ask her out now but, as others have said, potentially uncomfortable if she's not interested. Ultimately, it's up to you but it sounds like waiting a bit would be win-win. You sound very thoughtful and I wish you luck!
posted by smorgasbord at 6:36 PM on June 1, 2015
I don't think it would be morally wrong to ask her out now but, as others have said, potentially uncomfortable if she's not interested. Ultimately, it's up to you but it sounds like waiting a bit would be win-win. You sound very thoughtful and I wish you luck!
posted by smorgasbord at 6:36 PM on June 1, 2015
One more thought: I really do think the vibe is positive but I want to mention that "worst"-case scenario where Sean is the one she's actually interested in and/or he's under the same impression you are about everything. Or that she's just a very friendly, flirty individual whose gregariousness sometimes gets mistaken for romantic interest. Frankly, if that's the case and she's as kind as you say she is, she would politely decline your offer while trying to minimize any awkwardness on her part. Conversely, if she were mean about, then I think you'd be better off without her anyway. Fingers crossed!
posted by smorgasbord at 6:42 PM on June 1, 2015
posted by smorgasbord at 6:42 PM on June 1, 2015
Agree with the unanimous opinion, wait. Also, be particulary conscious of the fact that you may already be favoring her in your group sessions, which is annoying to everyone. It's very easy to do, speak to your favorite, romantic interest or not. It happens even in large lecture-style settings. The speaker will eventually be "talking to" only a small handful of the same people instead of the whole group and not realize it. If you haven't thought of this already, you're probably doing it.
posted by ctmf at 8:19 PM on June 1, 2015 [6 favorites]
posted by ctmf at 8:19 PM on June 1, 2015 [6 favorites]
The building consensus to wait is absolutely correct. But you can do things to improve the situation in the meantime. Be friendly, but don't cross over the "creepy" line. Flirt back. Banter. Have fun and keep any innuendo light and mostly PG-rated. And for God's sake, please don't do something clumsy like "confessing your feelings for her" while you're tutoring.
All these actions will help to build some positive sexual tension that will pay off for both of you when you go out post-tutoring. It's not like that chemistry will go away just because you're off the clock (in fact, it may be improved because there's no more question about whether it's "appropriate" for you to be dating).
posted by theorique at 5:21 AM on June 2, 2015
All these actions will help to build some positive sexual tension that will pay off for both of you when you go out post-tutoring. It's not like that chemistry will go away just because you're off the clock (in fact, it may be improved because there's no more question about whether it's "appropriate" for you to be dating).
posted by theorique at 5:21 AM on June 2, 2015
This thread is closed to new comments.
posted by wintersweet at 4:48 PM on June 1, 2015 [25 favorites]