Dear Captain Awkward,
There is a boy 2,500 miles away from me. We talk every day via text and average three hours on Skype weekly. We met online, and I promise, with details, it’s not nearly as sketchy as it sounds. Mutual friends and all that jazz. Since the beginning, it has been very obvious that we are flirting with one another. Or, at least, I am with him (friends say it’s being reciprocated, and I trust their opinions). Out of the blue, he has brought up stories about a girl he’s interested in who lives in his city that he is pursuing and who is not interested in him (from the information he has relayed- she gives one word responses to everything, she’s seeing someone an hour and a half away, and overall it honestly seems like she’s using him for attention, but I’m trying to be as fair as possible). After hanging out with her a couple times in the last week (all times he initiated and pushed for), she invited him to a concert that a band he likes was playing, and he declined due to ‘homework’ and spent the night talking to me on Skype instead. When I asked why he didn’t go, he just shrugged and said, “homework, and I didn’t want to seem too eager to hang out with her and make her sick of me,” something he obviously wasn’t at all concerned with up to this point. He acted evasive and changed the subject quickly.
Friends say I should just tell him I’m interested, but at this point it’s so obvious that I am that if he is, it would be really easy to just be all, “Hey I like you, you like me, let’s like each other in the open!” but he has not said anything like, instead opting for the confusing flirting, complimenting, etc. while saying he’s interested in this girl.
As a fun aside, the reason we started actually conversing was that he put in an application to be my cuddle buddy. If that is not flirting, my definition is way off and I should choose a new major.
What do I do? I do not want to just tell him I’m crushing on him pretty hard, because I like talking to him, he is very far away, and the idea of not talking to him is more sad than helping him get with a girl who he likes. What I want is to not be in this stupid grey area of “do you like me? do you not like me? are we flirting today? I am your advice-guru for the ladies?” I just want a solid relationship tag, even if its, “Hey, I like you. I want to flirt with you, but it’s too far away for an actual relationship, but were we ever closer, it would be on like Donkey Kong.” That’s it!
West Coast Worrier
If you’re looking for a flirty friendship and a sense of romantic possibility that you don’t have to actually worry about following through with in the day-to-day, keep doing what you’re doing, except leave out the part where you try to suss out what he *really* means when he says stuff like “I would like to be your cuddle buddy.” That sentence really puts the “b” in suBtle. If he said that to you, it is fair to say that what you have been doing all this time is called flirting.
If you want to put a label on what’s going on and/or suss out the potential for an actual relationship because you have desires and feelings that you’d like to put on the table, here are the words you’re looking for next time you’re in one of your marathon Skype sessions:
“It’s always so fun to flirt with you. It makes me wish you lived closer. Have you ever thought about us actually trying to meet up and date each other?”
There’s nothing wrong with wanting the casual flirty kind of relationship, btw, and that’s certainly more workable than something involving plane tickets (though there’s nothing wrong with wanting and deciding to have a dating-type-relationship either, or something in between). But self-serving “concern” for why things aren’t going to work out with his current crush and quizzing all your friends and friendly neighborhood advice columnists for what we all think is “really” going on will have to stop in both cases.
I think you want guarantees, and secretly you think that it should be on the boy to put the weird “I want to” stuff out there. No. And…no. It’s 2011. Use your words. Your wants matter. If he’s a shy woodland creature who retreats at the sign of a woman openly showing interest or even bringing up the question, he’s not ready for your jelly.