When Should I Ask For a Threesome?

You’re out to dinner with your girlfriend, enjoying a nice romantic meal. She’s having a great time, basking in the glow of your attention and the glass of red wine. You should be having a wonderful time as well, but you find that your mind keeps wandering as you eyeball a woman at another table.

It’s not that you don’t find your girlfriend attractive; it’s that all of a sudden all of those soft porn movies you’ve watched in your lifetime come flooding back to you and you’re sitting there picturing you, your girlfriend, and that other woman. Well, c’mon; you’re a guy, right? Now you’ve got a goal in mind. When should you ask for a threesome?

How long have you been dating?

There’s no proper length of time to wait until you ask your girlfriend (or wife) for a threesome, but you certainly wouldn’t want to ask a woman with whom you’ve just become involved. (Unless, maybe, she’s a full-time stripper; but even that is insulting. No woman likes a man who assumes.) Implying that your new date isn’t enough woman for you is a sure way to doom the relationship right from the start.

Additionally, if the two of you haven’t even had sex yet it’s pretty bad etiquette to ask for another person to join you in the bedroom. You’d be jumping the gun, just a little bit. Plus, you have no idea what kind of partner she is in bed. There’s a chance you’ll find that you’re more than satisfied with what she brings to the party.

If that’s not the case and you’ve been dating a year or more, and you’re pretty secure in the relationship, you might feel comfortable popping this kind of question. Perhaps she’s been turned on by the “50 Shades of Grey” series or she hasn’t freaked out at the hints you’ve been dropping.

How should you ask for a threesome?

Speaking of hints, the easiest way to drop this kind of bombshell gently is to rent a movie that involves some sort of threesome. Make sure it’s a gal, gal, guy threesome though or you might find yourself in a very awkward position when she grants your request.

During or after the movie, just casually say something about how fun it looks, and ask if she’d ever want to try something like that. The worst she’ll do is smack you and storm out, but more likely she’ll just say “no” if she’s not interested. However, she might very well be intrigued, and this simple, casual way of presenting it might lead to more interesting things.

Alternatively, you might just blurt it out one day – “Hey, I’ve been dreaming about two girls at once since I was a teenager. Have you ever thought about it?” What have you got to lose – sometimes the direct approach is the best approach for hard-to-discuss topics. This isn’t the kind of question that she’ll love more if you make it cute — you know, hiding it in a fortune cookie (“I see a ménage-a-trois in your immediate future”) or plastering it on a billboard.

Along those lines, don’t “woo” her with dinner and flowers to try to get her to change her mind. Leave the romance for romantic things; recognize that your desire for a threesome is more about desire than romance. Don’t ask her about a threesome when you’re in the midst of a twosome, or she’ll just think you’re insinuating that she doesn’t satisfy you in bed.

Who should you ask for a threesome?

If you’ve prepared yourself to ask about the threesome, you should do your homework and also have a few “thirds” in mind. But don’t make it too obvious or, again, your girlfriend will just think it’s simply an excuse to get into another girl’s pants while you’re pledged to the relationship with her. Only present your recommendations to your girlfriend if she asks, and mention them casually, as if you haven’t given it much thought at all (even though you’ve been mentally writing and editing the list for months).

Asking a friend can be very awkward and it can ruin a friendship whether the friend says “yes” and goes through with it, or says “no” and then feels equally uncomfortable around you both afterward. Instead, you can mention to the friend what you two have decided to do and ask if they know anybody else who might be interested. This way, if the friend is interested, she can volunteer the information. If not, the conversation can go towards other topics.

On the other hand, you can look to hook up with a complete stranger from a dating site, the classifieds, or Craigslist, but do your research thoroughly. Make sure you both meet up with the stranger in a public place and ask questions and set ground rules before any of you get physical. Be mindful of safety at all times, including health issues.

If you’re serious about wanting a threesome with your girlfriend or wife, make sure it’s for the right reasons and not just about selfishly fulfilling some teenage fantasy or beating a friend’s dare. Bringing somebody else into your relationship to share something as intimate as sex can be the beginning of an even stronger bond between the two of you if you approach it correctly and openly.