How to Date More than One Man at a Time

Date More than One Man at a Time

Emotionally, how can I date more than one man at a time?

Hi Ronnie The Dating Coach,

A good friend of mine is taking your Monday night teleclass and really enjoying it.  We were talking the other day about your advice to date more than one man at a time.  That would be fine for the first few dates, but we couldn’t figure out how to do it once we found someone we were interested in.  Wouldn’t that become logistically and emotionally complicated?  We are in our 60’s and noticing lots of single men in our age bracket, much to our surprise!  We’d love your advice on this please.

–Sixty and Sassy


Dear Sixty and Sassy,

Great question! Let me make an important distinction to help you understand the situation better.

Dating is not the same as being in a relationship.

My recommendation is not to get emotionally attached quickly because some men disappear and never call again. It’s hard to know which kind of man you are dating without a series of dates.

While you may have 4-10 dates with one man, that does not mean you are in a relationship with him. And you are not dating exclusively until you have that discussion. This is  a very common mistake in thinking that so may women make.

You are not in a relationship until you know you have a standing date on a Saturday night (depending on work schedules of course) without discussing it. When you just know you’ll see him Saturday night – then you’re in the first phase of relationship. How long this takes varies from couple to couple.

What I found both personally and with my dating coaching clients over the past 10 years is that many men simply disappear before you ever get to the first phase of relationship. Sometimes you only get one, two or three dates and then poof! He’s gone because he has opted out for any number of reasons. Or you might decide the man is not right for you and end things.

This is perfectly normal because dating is about getting to know someone to decide whether or not you want to spend more time together. I call this phase “data gathering” and make a joke about how that is the origin of the word “dating.” “Dat” comes from –  data and “ing” from gathering. When dating, you are in the process of discovering if the two of you:

  • Can have fun together
  • Understand each other’s sense of humor
  • Enjoy some of the same things
  • Have a similar world view
  • Live with the same value system
  • Carry a conversation easily, etc.

Stay neutral as long as possible
You want to stay as objective as possible at this point, especially for online dating. Yes, you may be excited and have feelings starting to build. But the longer you remain sort of neutral, the less likely you’ll go through those short but painful heart breaks if things don’t work out.

On the other hand, I agree it would be hard to be in a relationship with two different men. But that is not what I am suggesting at all!

Don’t focus on one man right away
Lastly, I don’t think you should decide to focus on one man until you get the idea from him that he wants to focus on you. And even then you might be cutting yourself short if you decide this too quickly. Keeping your options open until you get to at least date six is just a smart thing to  do so you don’t feel like you are always starting over if things don’t work out.

I personally dated 30 men in one year, dating several of them at the same time. (One time I was dating three guys named John!) I never knew which guy would call again so I dated as many men as asked me out if I was interested in them. Do you see what I mean? Don’t put all your eggs in “one basket” if you get my drift.

Many of your dates won’t pan out which is what makes dating more than one man possible. Some stick around, some disappear making room for new ones pop in.

I hope this has cleared up some confusion for you about dating more than one man at a time. Basically, it helps you hedge your bets as they say.

Have fun out there and enjoy those men!

Wishing you love,



Photo Credit: WhatsThatPicture

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.

1 thought on “How to Date More than One Man at a Time”

  1. Hi Ronnie,

    You’ve added just enough to this response to make it even more helpful than the one you sent to me. Thank you!

    I really like the part about “data gathering” and “dating.” The list of types of data to gather was great, and I’d love to see more. I have your book, MANifesting Mr. Right. Is that information in the book? It’s been a long time since I’ve read it. Maybe it’s
    about time to read it again!


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