How do I, as a 27 year-old Grad student invite women for coffee without them feeling it might be a 'trick-date', or having them not get comfortable?
Really, I want it to be a date _less_ than you do, but how do I convince you that?
To quote Always Sunny, it's all about the implication. I start with a question unrelated to the coffee "Jane, how are things going at Salesforce? I've been considering a move lately, mind if I get you a coffee and pick your brain a bit?" You can initialize the convo at that point and then either fluidly move the conversation elsewhere if desired, or, you know, not. Anyway, that's how I do it: transparent objective.
The converse is also true though, there's a much greater risk for not taking the leap given a). the amount invested (lack of it) so far and b). the real risk of them saying no (I mean if they say no, then what?). What if this person is the key that unlocks the meaning of life for me and I don't take this leap? Admittedly they're probably not but weighing these risks against each other, it would appear more foolish not to ask than to ask. If you don't ask, or you ask and they say no, you're exactly at the same position you are now (except your ego is a little bruised, but that'll recover). If you don't ask, you'll spare your ego potential embarrassment but you'll always be stuck where you are.
Please don't do this. Make your intentions very clear. "I find the fact that you love old botanic illustrations and go to flea markets every weekend to find them sexy about you." (where X is not her appearance, of course). "I'd like to buy you a coffee and continue this conversation."
If there is one thing my women friends may agree on, it is the ambiguousness of a meeting, particularly if they are interested in the person. Changing gender roles aside, the man has to take the lead. There must be polarity in the relationship from the beginning, otherwise it won't even start. This is the classic "friend zone", in which the window of opportunity exponentially fades away and trying to make the relationship romantic will burn the friendship.
Yes, the woman chooses if she wants to accept. Make it easier for her to say not. If she says yes to an ambiguous thing, she has to consider the possibilities. So, in fact, it may be easier for her to say no or give an indefinite "maybe" which is in fact a no.
One of my women friends who works in tech was lamenting recently about how guys would invite her to coffee wanting to learn more about her research. And then it would become clear that they just wanted an excuse to ask her out for coffee (a date). It is awkward for both sides. Consider this - if one of these coffees becomes a date or more, she fears word will get around that, yes, she will "date" people in her tech community.
Getting coffee with coworkers of different genders is such a completely benign and routine activity.
Keep calm and friendly when asking. Make sure the stakes are low for you.
Try ice cream.
Worrying about the outcome of this date/trick date/non-date probably isn't going to change the outcome of your conversation - it's probably not going to change her answer to your invitation. All it's going to do is worry you into not inviting her; and then what?
If she thinks you're an interesting person, she'll come for coffee, if she doesn't think you're an interesting person, she's probably not going to come for coffee unless you're more interesting than whatever else she's got going on right now... like studying for that exam she's procrastinating about not studying for... and really, do you want to be the guy (or girl) she has coffee with only because you're a distraction from her current reality or would you rather be the cause of the distraction?
The key isn't to appear interesting, it's to be interested and interesting. Start with the small talk, let her get onto a topic that fascinates her. Listen! Become invested in the conversation, find something you find fascinating about it. Offer insights you may have, walk, talk, get coffee and let life unfold.
... and if you don't mean it to be a date, why worry about it anyway? The outcome of whether or not she goes for coffee with you doesn't even make a difference. You may as well just say "hey, can we walk and talk? I'm not really finished with this conversation, but I need a coffee, perhaps we can walk in that direction" or if you're already walking perhaps "Hey, do you mind if we just stop in here so I can grab a coffee?" and then when you're paying say "hey, can I get you anything while we're here?"
The key is to be invested in the conversation. When you're invested in the conversation - not just your part of the conversation, but theirs too, people want to be around you. Being engaging is a key ingredient of that thing that everyone calls charisma. People want to talk to you because you make them feel important, you make them feel like things matter (not only to you, but to them as well), but mostly you make them feel; and I can tell you this:
A few days after, people may not even remember what you talked about, perhaps not even what you looked like, but they will always remember how you made them feel.
I feel like someone important may have said this before, perhaps Maya Angelou. Though I've held to this for years, so I like to believe she ripped me off (I'm deluded, what can I say? :D)
Often then you find that life will just unfold as you let it; and if you do find yourself in a position where you feel you have to make a leap, perhaps because you want it to become a date, or whatever, to rip a quote right out of a movie (We bought a zoo):
"You know, sometimes all you need is twenty seconds of insane courage. Just literally twenty seconds of just embarrassing bravery. And I promise you, something great will come of it."
Conversely - if you don't, where are you? You'll spend your life kicking yourself and asking "what if I had?"
You might as well tell a blind man the key is to use his retina.
Some of us find success at this sort of interpersonal interaction to be well-nigh impossible.
If you don't project what you're interested in, how are you ever going to know if they're interested in it? I've generally found that even the most arcane things I find fascination with, that you'd probably think people would think are boring can spawn the most intriguing conversations. If you project that fascination, that sense of wonder and awe, the thing, the grain of the idea that most excites you about it, when you get excited about it, people (in my experience) tend to come along for the ride. Before you know it, 15 minutes is 4 hours and all that stuff you wanted to get done this evening is gonna have to wait until tomorrow.
Not a woman, but I suspect this is true & a good point. Coffee is ambiguous, and it seems unlikely you'd be turned down because I would probably enjoy hanging out with you but this MIGHT be a date so NO.
She (or he) might wonder "is this meant to be a date?", but you can concretely answer that question just in your behavior. The way you act will telegraph your intentions. Stammer a compliment about her/his eyes, it's a date. Wave them over to your table when they walk in, say hi, don't even get up, it's just friends.