Tuesday’s Topic: Sleeping With Two People

By David Wygant

Let’s go a little further today and talk about sleeping with two people at the same time.  I’ve got to admit, I’m guilty of it myself.  While I was dating heavily in my 20s and even a bit in my 30s, I did sleep with two people at once.  No, get your mind out of the gutter-I did not have a three-way.  I wasn’t sleeping with two women at the same exact time, but I was dating and sleeping with multiple partners at the same time.

At the time, I found it fun. I found it exciting.  I enjoyed it, but be forewarned that it’s not something for everybody.

Some people, even if they want to, just can’t do that emotionally, mentally, physically, whatever it might be.  Some people think it’s what they want, but then they have trouble being truly intimate with either of the people they’re with.  A lot of people also can’t keep track of it.  One client of mine began sleeping with two women because he wanted to try it out, and we talked and worked on it, worked on a lot of the mind set that’s involved in it.  And of course, in the middle of sex, he called out the wrong woman’s name.  Some guys just aren’t built for it.  Some guys need to focus their attention on one lover at a time.

I’m a firm believer in doing whatever you want.  I really am.  If you want to sleep with five people at once, if you want to have an alternate lifestyle with your spouse, if you have multiple sexual partners, I don’t care.  You do what makes you happy.  I’m not somebody who’s judging.  I’m not here to tell you what to do with your life.

I’m somebody who can advise you.  So if you really want to sleep with two people at once, you’d better have that personality, you’d better be able to keep track to what you said to each of them.  Because it’s not fair to your partner if you blurt out, as my client did, the wrong woman’s name in the heat of passion.  You may consider yourself a player, but I certainly don’t think it’s cool at all when you can’t keep track of what one woman is about on a deep level and then, during intimate conversations, you mix her up with another woman you’re sleeping with.

So, if you are sleeping with more than one woman at a time, I think you need to really be present with each of them at that moment and give them your full attention because it’s not going to last forever.  Eventually, one of them is going to win out.   Eventually, we all develop more feelings for one over the other.

When I was sleeping with multiple women, I worked at really doing this. I was always present with the woman that I was with.  I always enjoyed her time.  I always kept my story straight, and I always remembered what she was about, I remembered our intimate conversations because I really cared about understanding her.  If I was sleeping with more than one woman, I was having a good time.  I was enjoying it.  I also knew that there was a possibility that one of them could win out over the other in the long run.  One of them would just stand out more to me, and my relationship with the other would be less meaningful.  Maybe they were sleeping with more than one man as well.  What does it matter?

But what really matters here is you’ve got to keep it straight.  You’ve got to understand yourself and your abilities.  You’ve got to remember what happened with each one and keep each a very separate, beautiful moment.  And that’s the mature way to make this happen.




  • I don’t mind it, but I have a few conditions: a girl that I date is just for fun and I come clean before getting intimate with her. I let a girl know of my intentions and lifestyle very early in our relationship.

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder Badonlinedates.com LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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