Curious about having a threesome - how can I approach this couple?

Dear Dan and Jennifer, I'm 34 years old and have recently won a 3 yr battle with cancer. I have a new lease on life and want to live it to the fullest.

I have an absolute best guy friend, “Rick”, who is dating my best friend “Abbie”. I have been thinking a lot lately about having a threesome with "Rick" and “Abbie”. I'm just not sure how to broach the subject with either of them. "Rick" and I have joked about it a few times before but I always brushed it aside…

Now, how should I go about approaching the subject for real? I love them both, and I don’t want anyone hurt at all.

[Greg69Sheryl]

Trying to initiate a swinging experience with vanilla friends can be hazardous to your friendships, so you have to ask yourself if your fantasy is actually worth the risk of losing your friends. If you really want to have a threesome, your best bet is to visit your local swing club (many clubs admit single women for free) and/or place an ad on a swingers website.

However, if you are as close to this couple as you say, the next time you joke about it with Rick, try asking him, "Seriously, would you and Abbie ever consider having a threesome with me?" If he is not comfortable with the idea, or if he feels that Abbie wouldn't be comfortable with it, hopefully he will be honest with you. But, as we said before, this approach involves a certain amount of risk. If Abbie is prone to jealousy, she might interpret your proposal as a way of trying to steal Rick away from her.

Whatever you decide, we wish you luck.

[Ryan S.]

Could really put a damper on your friendship IF any of the three of you are not careful.

But, if everyone is careful this could work out very well. Or somewhere in between.

Approaching Rick may seem easier. But here is where that could contribute to the negative side. We already know through joking around with this that Rick may be into the idea. He could talk to Abbie for you and see if she might be in to this. Easier, but a little more risky.

I think the best approach would be to go to Abbie yourself. Tell her you feel more comfortable to do this with people you both know and trust. If Abbie does turn out to not want to, or has a bit of a jealous streak at least she would know that you didn't make a move on Rick without her knowledge. She'll also know you will have approached her first with the actual and serious proposition. And that you understand that they are together where if she says no, no further moves will be made.

What Rick doesn't know won't hurt him at this point. It could hurt him indirectly if you went to him first and Abbie refused. She may then start to question her and Rick's relationship because of you. It can most likely either end your friendship or their relationship badly. Possibly both. This gives all of you an out if Abbie is uncomfortable with the idea.

She may not understand quite as well if Rick alone approached her on the subject. If it goes well, then sit down with the both of them and talk it over. If it doesn't go well, never bring it up again.

Through some fairly extensive swinging, I've learned that the women very much rule the kingdom. At this point it'll be Abbie's decision to continue or stop and will always remain so. Don't bring it up with Rick any more (even jokingly) until you have talked to Abbie.