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. You want to wait a while to find out if a man seems trustworthy, is compatible, and has long-term potential.

You also want to see if you can tell if his relationship agenda matches yours. In other words, is he not looking for anything serious and just wasting your time?

One big giveaway is if a man actually says anything about not wanting anything serious or not looking for a relationship, but is willing to get to know you and see what happens. That is a red flag letting you know you do NOT share the same objective.

Waiting also helps you avoid sleeping with several guys at the same time which might not be the best choice emotionally or physically.

The Oxytocin Cloud

Now I realize 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 the guy 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 wanted to avoid sleeping with a guy and never hearing from him again, which I knew would be heartbreaking.

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 as I was deciding if a man had real potential for lasting love.

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

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 and take care of myself emotionally.

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 TV’s 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.

However, be careful. I’ve had clients say this on the third date and the men would agree to exclusivity just to get them into bed. Date #3 is too early to determine if you should be exclusive, even if he readily agrees. You may be highly attracted with chemistry off the charts, but you do not KNOW him yet. Waiting a few more dates is a safer path where your heart is concerned.

3) A More Feminine Approach

When exclusivity has not come up after a string of dates, I’ve suggested my clients try this softer approach to bring the topic up. Try saying this instead, “I’m looking for a committed relationship. Men are still connecting and asking me out 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 because it gives him the opportunity to claim you and this idea of not seeing others.

If that doesn’t work, he might not be the right guy, or he’s just not ready or interested in a monogamous relationship.

The Choice Is Yours

So, the choice for sleeping together is up to you. 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. Some women are fully capable of not getting attached.

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 casual and not looking for anything serious or monogamy. Again, this leads to disappoint at the least and possible heartbreak.

Serious about Lasting Love?

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.

You want a man who is available and makes an effort to spend time getting to know you. If a guy has such a hectic schedule that he can’t find time for you at the start of things when it’s the most exciting, that doesn’t bode well for your romantic future. Walk away.

Don’t fill your time with men you consider to be “place holders” because you have no one else. This clogs up your energy and takes you off your path. And you might still unwittingly fall for the guy and feel attached, ending up with the wrong man.

Hope that helps clear things up for you about sleeping together if you are serious about finding “The One.”

Wishing you love

dating coach, find love, meet men





Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

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