Your nerdy best friend has a crush on cutie; cutie asks you out. What do you do?

Today’s hypothetical is about Dave, Don, and Jenny.

Dave and Don are college sophomores. They are both roommates best friends, having known one another since kindergarten; each considers the other his brother by another mother. Dave would never had made it through any of his high school math classes without Don’s help. He returned the favor by protecting Don from bullies in all through high school. In college they find they need one another less on a practical level, but that doesn’t matter; they genuinely love one another.

For Dave, college has been an unabashedly wonderful experience. He’s tall, built, handsome, and charming, and has happily gone from girl to girl. Don has not been so fortunate. He’s not ugly by any means, but he’s terribly awkward and shy. There’s been many a night in which Dave has listened to him bemoan his inability to get out of the friend zone with women. Dave would cheerfully and viciously mock anybody else who said things like that, but not only does he refuse to do that to Don, but he won’t tolerate others mocking Don thus in his presence, whether Don is around or not. He loves him, after all.

In the fall 2010 semester, Dave and Don take a course on Chaucer together; it’s outside Don’s major but he needs it as an elective, and as Dave is good at stuff like that, he enjoyed the opportunity to help Don out academically for once. Among their classmates was Jenny, who, like Don, had some trouble mastering the material. The three of them take to studying together, and Dave quickly realizes that Don was attracted to Jenny. So is he, but he doesn’t want to get in his friend’s way (and is getting plenty of action elsewhere anyway), so he never makes a move.

The semester ends. While all three of our characters are native to the same city they attend school in, Dave goes away for winter break, while Don and Jenny both stay home. Before Dave leaves, Don says that he’s more attracted to Jenny than he’s ever been to any other woman, he says. Dave encourages him to go for it, and soon; he’s got Jenny’s email and phone number, after all, and there’s no sense in waiting. Don says he’ll wait till the next semester to make his move.

Returning to campus after winter break, Dave runs into Jenny in the bookstore. Don is not there. They chat about their break, and Jenny mentions that there’s a party being thrown in her dorm on the first Friday night of the semester; she invites Dave to come with her. Dave hesitates, then asks if she wouldn’t rather go with Don. Jenny frowns at that. "I’m tired of waiting for him to make a move,’ she says. “I like him and I would’ve gone out with him if he’d asked me last semester, but he’s had plenty of time and plenty of opportunities and he’s wasted them all. If he doesn’t have the balls to ask me out, I’m not interested. Anyway, you’re cuter. So are you coming with me or not?”

What should Dave do?

Jenny is fair game for Dave if, — and this is a huge IF, he’s up front and open about it. If he can’t tell Don directly that Jenny asked him out and he said yes then he has no business accepting the invitation.

Of course I’m of the opinion that Dave should tell Don about the exchange no matter what. If he wants to accept the offer and risk losing Don as a friend, well, that’s his choice to make and I’m not going to criticize him either way he goes.

I picked “Tell her he has to check”, but the real answer is that the matter calls for subtlety and sensitivity. It’s like everything else—you deal with it.

Then again, I’m not a competitive dater, so hey.

Could you tell us which of your scenarios is real and which is “my friend wants to know?” A friend asked me about this.

In your scenario, Jenny has misstepped. She has waited patiently for Don to ask her out but is willing to make the move on Dave.? Dave needs to give her the “let’s be friends” speech and maybe ask her about that.

Note: Option four should read: “Say yes and tell Don why. That’ll definitely teach DON a lesson.”

I do not mean to imply that Jenny needs a lesson taught her.

Do you not know the word hypothetical?

Also, I’m 40 and way past this point in my life.

I’d say Dave should go out with her if he wants to.
Why should Don and Dave be deciding who Jenny is going to go out with?
Jenny decided for herself who she wants to go out with, Dave.

Dave is not deciding whom Jenny may go out with. He’s deciding whom HE will go out with. After all, he has the right to turn Jenny down for any reason, doesn’t he? (Just as she has the right to turn HIM down for any reason).

As for why Dave should decline, it’s obvious to me. Jenny’s a girl he knows from class. Don’s his oldest friend and he loves him.

I picked other. I would turn her down gently(maybe GF who lives in Canada would come into play), but recommend she ask Don. Clearly she’s willing to make the first move, so there’s no reason for her to wait around on Don to make the move. If she’s ready to get into a relationship, and there is no reason she wouldn’t go out with Don(as per her statement), then why not direct her towards fertile ground?

Enjoy,
Steven

Definitely the 4th one. You snooze you lose. The mentality of Don was too highschoolish, ‘ooh i have a crush but i’m scared to ask’. That’ll teach him a lesson, he can get the sloppy seconds.

Reminds me of the parable in 2 Samuel 12.

I picked other, as in cute chick asks you out - you go and you enjoy every minute of it, if you want to, that is.

I said “okay” when she asked me to prom, then called “Don” to tell him and helped him think of someone to ask to prom himself. And then got him to actually ask her. So I voted accordingly in the poll here.

(25 years later, still friends with “Don” and with girl who asked me to prom. :slight_smile: )

I answered that I’d delay saying yes while asking for permission but now that I’ve thought about it a bit more I’d just say no, considering the friend is planning to make his move.

So yeah. I’d turn her down.

If Dave did not have the choice of any girl, then I’d be fine with him embracing this opportunity. But he does–and this girl would just be one of many, and thus unimportant to him. She is important to Don, and Don is important to Dave, so Dave should do what he can to help Don, which, in this case, is turning her down.

If Jenny wants to teach Don a lesson, let her do so on her own without including the betrayal of a friend. You only teach someone a lesson in that hamfisted manner when it’s the only way left to get through to them. And it isn’t, since Don is willing to do what he needs to do.

The one think I might do is tell Don about it, and encourage him not to go out with a girl that wants to be that controlling. But I would give her the benefit of the doubt that she was only trying to rationalize her feelings. Of course, that means she likely will turn Don down–she merely wants to like Don.

I think I would feel like Jenny is a game player. With Don she’s all demure and shy but she can ask me out directly, oh and I was the cuter one the whole time? Whatever.

I didn’t even think about that. You’re right.

What a douche.

Why isn’t there an unqualified “yes” answer. I bang her. What’s the issue? She has no relationship with Don, and he has no ownership over her. Don can kiss my hairy ass.

Tell her to find one of her slutty friends for Don. He just wants to get laid. If that happens, he’ll forget about Jenny as fast as you do after you bang her.

I would say no thanks to Jenny, and go tell Don that Jenny is interested in him and for the love of God, would he please just ask her out already?