Sleeping Together: What if You’re Dating More Than One Person?

Thinking about sleeping together, but not sure when the time is right? Dating more than one person? Here are 3 tips for handling intimacy .

Is the Timing Right to Sleep with Him?

sleeping together, dating coaching, dating coach, first date sex“Hi Ronnie The Dating Coach for Women,

I really enjoyed the teleclass about how Patti found love. Thank you. I wish you had a chance to talk about sleeping together and how you handle it when you’re dating multiple people. When  it’s a few months in – are people having sex with multiple partners when dating more than one person? That doesn’t sound like something I’m up for. So what should I do?

Thanks for your help!”
Good Girl


Dear Good Girl,

Glad you could make it to my teleclass with my client Patti who found love.  This is a great question and would have been good for the Q & A portion of the call.

For the most part, I doubt a lot of single women over 40 are sleeping with multiple partners. However, I have three methods to help you handle this big question of when is the right time for sleeping together.

1) Holding Out


Many women hold off before sleeping together to prevent getting emotionally attached prematurely before you know if a man has long-term potential. Waiting also helps you avoid sleeping with several guys at the same time which might not be the best choice emotionally or physically.

Now I realize that it’s not easy to wait, but it sure makes things easier emotionally. When you take your time before sleeping together, you give yourself a chance to get to know a man without your hormones (oxcytocin) kicking in and clouding your judgement.

When I was dating and seeing multiple men simultaneously, this overlap of guys rarely lasted. Most men disappeared after one, two or three dates. I waited at least for the sixth date to sleep with a guy because that showed me a man was consistently pursuing me.  I interpreted this as him having genuine interest.

In addition, after six dates, we’d spent many hours together, so it was easier to decide if he was a good risk. I did this because I wasn’t crazy about sleeping with a guy and never hearing from him again.

This Is Not Game Playing

Holding off for date six worked well for me. By that point, the field had narrowed as many men dropped away. This was a huge help to stay objective about a man as I was deciding if he had real potential for lasting love.

Some women worry that a man won’t want to wait. My dating advice is that if a man doesn’t want to wait, he’s probably not the right guy.

Understand the point of waiting is not to play a game; it’s about guarding your heart. Most women start to bond after sex which is a natural response. I chose to wait to guard my heart.

2) Waiting for Exclusivity

Another way to handle sleeping together is to wait until you discuss and agree on exclusivity. That’s the dating advice Patti Stanger, Bravo TVs Millionaire Matchmaker gives. Patti says this is what you tell a man when he suggests intimacy, “Oh, I don’t sleep with a man until we’re exclusive.”

This sets a clear boundary around sleeping together. You are not asking him to be exclusive, simply stating the facts of how things work for you.

3) The Feminine Approach

When exclusivity has not come up after a string of dates, I’ve suggested my clients try this soft approach to bring the topic up. “I’m looking for a committed relationship. Men are still connecting with me online. Do you think I should close down my profile?”

This allows a man to come to the conclusion of exclusivity on his own. This is a gentler, FEMININE approach and if that doesn’t work, he might not be the right guy. Or he’s just not ready for a monogamous relationship.

The Choice Is Yours

So, the choice is up to you for sleeping together. A lot depends on your emotional makeup and strength. Any of these three approaches can work to keep you from jumping in the sack before you are emotionally ready.

If you’re dating several different men casually, and there are big gaps in time between dates, that is another story. Casual dating means you don’t plan to get attached to anyone. However, if you’re serious about finding lasting love, my dating advice is to avoid casual dating.

Women will often fall in love after enjoying a sexual relationship and then have to deal with the fact that they are dating a man who is more casual and not looking for anything serious or monogamy.

Serious about Lasting Love?

So, when you are serious about finding lasting love, avoid casual dating or dating any man who can’t see you at least once a week. That’s a sure sign he’s not serious about finding love or you.

Hope that helps clear things up for you about sleeping together!

Wishing you love

dating coach, find love, meet men





Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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