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!
halp.
Sincerely,
West Coast Worrier
Dear 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.
CaptainAwkward.com 
Out of curiosity, what exactly is it like on Donkey Kong?
Ask and the internet will provide: A brief history of the phrase “It’s On Like Donkey Kong.”
I blame Ice Cube:
May I also recommend the documentary The King of Kong: A Fistful of Quarters, in which it is on EXACTLY like Donkey Kong?
Trace Adkins would also like you to know that she’s got it going on like Donkey Kong.
Another thing for LW to consider in re: it’s 2011: you don’t have to apologize for meeting someone online. It happens a lot. People online are also people in real life.
signed,
I married the dude I met online
I have… multiple friends who met and got together with people they met online! And probably three-quarters of my best friends are people I met through the nerdiest of online venues (roleplaying games, fan forums, and fanfic). This is only an issue when I want to give them hugs or share the awesome pie I have and they are a six-hour plane ride away.
Look how we’re all meeting each other online…RIGHT NOW.
There isn’t a regular commenter that I would not want to have a beer with someday.
In a well-lit public place.
Next week sometime?
Mmmm, beer.
*STARE* Hi. *STARE*
A VERY public, VERY well-lit place for you. 😉
Hey, if your captainly rounds ever bring you to the fine city of Boston, there are many fine pubs and bars here!
Ditto!
I was thinking the same thing. My current girlfriend and I met online and we’ve been together almost a year. Contrary to what Buffy teaches us, they don’t always turn out to be demons living in the Internet. Only sometimes.
Agreed. I met my girlfriend online and we’ve been together over a year.
I don’t want to call the fear of predators and such “paranoia” because there really are predators, but there are reasonable precautions you can take (meeting in public, etc.) that bring the danger level down to the same level as meeting people offline. Your college classmate could also be a predator, after all, for all you know. (Probably not. Just saying, interacting with humans always involves an element of risk. That’s not going to go away.)
I think you’ve got to ask yourself what your end game is here. Do you really want to date this guy long distance? If so, then you need to follow the Captain’s advice and tell him that. But if you just want to keep flirting without trying to transition that into a relationship (because of the distance, or because you’d rather not risk the friendship, or for whatever reason), then I’ve got to strongly discourage you from trying to have a Serious Talk in which you try to get him to admit that although you’re not going to date he does in fact Like You.
Trust me when I tell you this: those talks are hella overrated. They kill the fun bantery sexual tension and instead lead to either deep angsty misery about how fate has conspired to separate you, or they lead to him saying that actually he doesn’t Like You and then you still lose the fun flirty thing. Because honestly, you can’t tell from someone’s Skype flirtations whether they want to date you. Some people are just flirty. And some people maybe are flirty because they “like” you, without that meaning they want to date you. And no matter what he says, you will spend weeks or months or years (yes, years — again, trust me) dissecting it and having more Talks about it and listening to Snow Patrol sing about it, and that is no way to live.
If you’re having fun flirting, flirt. And if you want to date, tell him that. But if your end game is to spend a lot of time angsting with this guy you’re not going to date about how you might want to date in another world? You have better things to do. I promise you.
VERY GOOD POINTS. Long distance relationships are exhausting, especially when there is no definite “this is the day we move to where the other person is” date in sight.
A 2,500 mile away cuddle buddy? Really?
That makes me sad.
“Use your words.”
Best. Dating. Advice. Ever.
Actually, life advice, too.
I remember making fun of people with “online friends” back in 1995. Now many of my best friends are people I met online first (though later in person). 2500 miles is a huge distance, but hey, flirting is fun.
I was in a similar situation in college, with the one real difference being that we were at school together, so he was physically present in my life. After pining and talking to everyone but him about my feelings for 2 years (during one of which he was overseas) I finally sent him an email saying that I liked him, and would appreciate it if he didn’t seek my advice about other women he was interested in because it was too hard for me to have those conversations. I then disconnected from the internets for a couple days because i really didn’t want to see his reply, and snapped at my sister for asking me about it, such was my anxiety.
He wrote me back saying whoops, he didn’t know that, and he was sorry if he’d made things hard for me and could we still be friends. And you know what? It was actually totally fine. I sent the email hoping i would get some sort of “finally, our stars are aligned, together 4ever!” response, but instead I got EPIC CLOSURE. I saw him when we started senior year a couple months after the email, and I was no longer into him, at all. Which was great. We stayed good friends for a couple years, until we parted ways for other unrelated reasons.
Point: I was honest about my feelings, and got an unexpected response that (eventually) totally worked for me. It was hard, and it sucked for a little while, but it actually turned out really well. I can’t promise that will happen for the LW, and I’m not suggesting closure as a cure-all — that just happened to be what worked for me. I think telling him what’s up with you can’t be worse than angsting in private to no avail.