Eesh. I guess. But it will also provide fuel for that classic straight-guy stereotype - "why do I only get hit on when I'm already in a relationship?"

If he dumps his girlfriend for you, LW, you've got to at least give him a chance to date you properly.

It probably can't hurt for LW to say, hey, if we're ever both single at the same time, we should enjoy an FWB arrangement. However, I disagree that she should date the guy if he dumps his on-again, off-again girlfriend for her. If a guy dumps someone else for you, chances are he'll dump you for someone else.

Good luck!

Dan seems to assume that to make the offer is to suggest that the dude immediately break up with his girlfriend. I don't think that's necessarily the case.

I've heard that offer when I was with someone, and didn't think it suggested that I break-up with my then-girlfriend. And when that relationship ended a few months later, I called up my friend and banged the hell out of her. Worked out for everyone.

Orrrrrr.... You, LW, can grow up, stop being nostalgic for the forbidden fruit of years past, and go meet someone who doesn't have a shitty relationship that you can selfishly force yourself into.

@4: Whaaaaaaaat, how am I going to stunt my personal growth if I stick to healthy relationships?

what @4 said.

LW. Going against trend, I agree with Dan. If this guy was in some cosy, never to be torn apart relationship- I'd say stay away. Do not tempt him.
Given its on/ off/ on/ off- it doesn't sound like it's that committed.

On-again off-again relationships are off when they're off. Telling someone you're interested next time it's "off" is fine; a relationship that's currently "off" isn't a monogamous relationship, because you can't not date someone and expect them not to date anyone but you.

@7: "Given its on/ off/ on/ off- it doesn't sound like it's that committed."

And all the more drama reflected upon yourself. Some people are serially drawn to the smouldering husk of dying relationships, it's not a great sign. If he expressed any independent interest he should be encouraged to leave and pursue, but I wonder if she's not drawn more to the damage than she is the man himself. She should still butt out and not make excuses about why he's a good target for her while he's in a committed relationship, even if not her ideal.

Jesus christ Dan, really? We've progressed to encouraging people to actively hit on people who are in relationships now? That's messed up.

"Hey, when you get a moment, it would be super-duper if you could start banging me. Think about it - thanks."

My advice to the LW would be to increase the likelihood that you would hear about the next off-again cycle sooner rather than later. That might be through a mutual friend, Facebook, or Twitter, but don't stalk. Step back, relax, and wait your turn.

I think it would make more sense to keep the offer light, rather than to make it explicit. So I'd probably say, "Wow, I have a lot of regrets about the fun casual sex I turned down due to my misguided religious upbringing," and look him right in the eyes. "Wish I could have some of those opportunities back again." Then look down at my drink.

Why anyone has a problem with someone hitting on their mate is a completely alien concept to me. Of course it may be different for women than it is for me (women getting more or less continuous sexual attention versus my never having been hit on --not once-- in 50+ years.)

"I would usually wait until he actually was "off-again" but by the time I hear that he's broken up with his girlfriend he could be back together with her again or with someone new."

Yeah... Get it, girl.

Or as so many people have said, maybe consider leaving this one as a fantasy because this guy sounds flaky and prone to drama.

EricaP - of course you're right. I retract my comment above.

The part that got glossed over a bit is that this guy is a *family friend*. From the sound of it, the families are pretty close, which makes hooking up with the dude a bad idea. That goes double considering the LW's family is comprised of conservative Christians (presumably his family is too). That next family vacation is gonna be awfully awkward.

I dunno, too much potential drama for my taste. I wouldn't do it. Move on and find someone else who's not basically your cousin.

Odd. In today's Savage Love column Dan recommends tactful disclosure of FACT having cheated on his wife, and thus the relationship ending. When it comes to offering a FWB relationship to someone in an on-again-off-again relationship no mention of being tactful. Not that this is a problem or a mistake by Dan, just a notable contrast.

To WTFTF, I would suggest a less direct approach than "come fuck me if you become single again." Instead, mention to him that if he enters an off-again period he should give you a call since you feel a little more relaxed about hanging out with him during those time periods. THEN, once he lets you know that he is single, tell him "come fuck me now that you are single again."

Agreed @12. I think patience will go a long way with this one. It may seem SO IMPORTANT to bang THIS guy RIGHT NOW, but cooling your heels for 6 months or a year could have a big difference in her desires for this dude. Especially at 22 a lot can change in a few months. Stalk him on fb and go out and date other people.

@17: "I dunno, too much potential drama for my taste. I wouldn't do it. "

Well, you're not addicted to highly drama-tinged situations, now are you? :p

"Some people are serially drawn to the smouldering husk of dying relationships, it's not a great sign."

And some people are serially drawn to the one they can't have. They sound like a perfect-for-each-other clusterfuck.

I guess it depends in part on whether forbidden dude is going back to the girlfriend because he's addicted to drama, the girlfriend is manipulative, or he's very lonely. If he's addicted to drama, bad news. If he's susceptible to manipulation (at 24, quite likely), he needs to get over that. If he's just lonely, he may do a lot better if he knows there are other offers pending.

I once got out of a very nasty relationship, in part using as a crutch the knowledge that someone I knew had a huge, obvious crush on me. Hadn't acted on it, because he was a gentleman, but I could tell. That gave me enough hope that I was able to move on without fearing the void of being alone. (The ex was one of those isolation-inducing types that had a meltdown if I spoke to anyone else.)

LW, take a chill pill, as we used to say in the 90s. Wait til the "off-again" phase, and if you miss it, no big. Not wanting to miss out on sex is not a good reason to be a jerk.

it is not a favor. I'm not sure why the inconsistency on this one Dan.

It might be "on-again, off-again" because they're working through issues. My current relationship is of that nature. I can say for a certainty that having some opportunistic person inserting themselves into the already existing conflict that is hellishly difficult to resolve, would probably torpedo things altogether. How can people work through the difficulties that every couple faces if there's some new, fresh, exciting temptation just waiting with bated breath to come and snatch up one of the people while they can? Be classy. Treat people the way you would want to be treated. Happiness cannot come by trashing someone else's relationship....because even if it's on its way out, people need closure and to be sure that ending it is what they wanted.

"because even if it's on its way out, people need closure and to be sure that ending it is what they wanted. "

Unless they have already ended it umpteen times, in which case they may appreciate a bit of help to break things off permanently this time.

@22: No doubt. I've been there as well, but the motives of the LW are potentially questionable, is she trying to avoid delayed gratification? Does she really care about what's best for the guy? A rebound/fling could be healthy or messy but the more she actively participates the more she's responsible for the outcome on some level. It just sounds way too excited and not wary enough from her tone.

@25: Closure is created by individuals and in reality rarely if ever achieved through mutual consensus.

I'd say as long as you are tactful go for it. I don't really see the drama that other people are talking about. You mention several times about being open to rejection, doesn't sound dramatic, sounds pretty reasonable. And if you are as open to rejection as you say then he should have no problem just saying no. If they broke up I doubt it'd be because of you. Someone that I fooled around with a few years ago told me they'd fuck me if I were single again? Should that really be their responsibility if I break up with my current partner? How would the old partner be responsible at all?

I've been in a similar situation and kept quiet. It's not that I regret not having the sex I wanted (there is always great sex around the corner) but I do regret not at least trying, always wondering what if. You say you're homoflexible and don't find many dudes attractive, so if it were me I'd speak up and saying something to this particular dude. Again, tactfully. The other commenters gave good advice on the tactful front

Undead, she says she found him hot long ago. Not just since his current situation was running hot and cold.
And she says she doesn't find many men hot.
Ok. Just get someone on the inside to alert her when it's off again, then she tell him.
On/ off/ on/ off relationships are usually doomed, unless a big learning for both happens.

@30: Doesn't make her current obsession any healthier. He hasn't had a girlfriend the entire time she's known him, she had plenty of chances before this point then. And as a family friend she'll have chances later on.

Undead. This is not the therapy couch. The girl is hot for him now.
I still think she should go for it.
If, if this man is bent on working it out with his current on/ off girlfriend, then he'll just say no.

@31 I think the point is she had chances and didn't take them bc of her religious upbringing. sounds like she recently left that behind and is trying to make up for lost time, hence the "obsession". I bet if she just said something it'd feel less urgent bc she said what she needed to, making up for times she said/did nothing, and the ball would be in his court

I knew a guy in school who was in an on-again, off-again relationship with a girl. From what I could tell, she was controlling and demanding, but hot in bed. I really should have offered to bang him if he were single.

We can't tell about this guy and his girl. Maybe they really are fundamentally good for each other, and just working through issues--in which case, an offer to bang someone else shouldn't break them up. But maybe they are fundamentally bad for each other, and keep going back out of some kind of fatal attraction--in which case, the chance to bang someone else, someone friendly, might be a great way to finally get out.

I see no harm either way. Make the offer, keep it light, and don't sit around waiting for him to call. Just see how it goes.

As for the "don't bang him, he's a family friend" theory: I have some sympathy for that, it carries high likelihood of making things awkward later. But the thing is, everybody is somebody. You meet people at work, through family, through friends. If we didn't allow ourselves to bang anyone if it might make something awkward later, the race would die out.

@34: "But the thing is, everybody is somebody. You meet people at work, through family, through friends."

It's not that so much as the combined wanting to seek him out while he's still actively entangled in a complicated situation. The totality makes it a bad idea, not dating a coworker or family friend sort of situation.