Dating After Divorce: Should I Date More than One Man at a Time?

Now this is a FUN question!

Dear Dating Coach,

I’ve been dating Max for nearly a month and it’s been fun. He emails and texts quite a bit, and also calls, although not as often. We see each other 2-3 times a week and things are going pretty well. I’m not ready to get exclusive – just taking things slowly since I’m just out of my 15 year marriage.

There are a few things I’m not sure about and time will tell how they play out. For one thing he’s in his late 40’s and never been married. That makes me question if he will ever commit. Another is that he’s not crazy about animals and I have two dogs and a cat. We spend most of our time together at his place as a result. Last, I’m starting to question if we share the same ideas of lifestyle. I certainly don’t expect fine dining every time we get together, but eating a proper, healthy meals is important to me and he’s fine with chips and salsa.

To complicate matters, he’s away on a business trip for two weeks and in the meantime, I ran into an old boyfriend, Jack, who asked me to lunch. I went, we had a fabulous time and he asked to see me again.

So enough background. The question is – can I date them both?

Thanks for your help,

Dear Lacey,

First off I want to thank you for reminding my readers that it’s an abundant world out there – you have the opportunity to date  two men! How nice.

The point of dating as I see it is to gather data about the person to see if there is long-term potential. And that is what you are doing with Max. sometimes what seems like a great connection unravels with a bit of time as you see you need more than attraction to  make a good relationship last. If you don’t not have the same values or principles about how you want to live, that can be a deal breaker.

I don’t have an issue with Max adjusting his profile since you two are not in an exclusive relationship. If you were, I would expect both of you to take down your profiles and focus on each other. But since that is not the case, it’s hard to limit his freedom – or yours.

If you want to eat better than Max does,  bring this up and tell him it’s important to you. Good relationships are full of compromises and you might as well start discussing things to work them out now. If you find he is unwilling to compromise, then you have learned something about him and his long term, Mr. Right  potential.

Regarding your animals, sometimes people adjust to animals, sometimes they don’t. It’s hard to say. But if you want to spend more time at your house, invite him there and observe his reaction. This is more information about his potential.

Since you have no exclusivity arrangement with Max, why not date Jack too? Spending time with Jack will not only help you get to know him again, but will also help you understand what works for you and what doesn’t regarding both men. Gathering more information in this case is a smart move.

This advice is based on the initial dating phase which usually means the first 4 to 10 dates or until you know you have a standing Saturday night date which signifies the firs t stage of relationship. This upfront period is when things are far more casual and free from expectations. It might be a lot harder to date both men longer term as feeling will build and intimacy will deepen. The last thing you want to do is end up in a situation where you are deceiving one or both men about your extracurricular activities.

I can’t provide the cut off date or how long this should go on. but I think you will know what is right for you and will make your choices accordingly. From my perspective, dating in multiples is a smart strategy to find the love you want. Things often crumble or disappear after a few dates which is to be expected and perfectly normal.

Many women fall into the trap of serial monogamy which means they stop dating other men after one or two dates to focus on the one man. This is not always the wisest move since you can end up with a man who doesn’t meet you rneeds because you  got too wrapped up and involved before you finished the courting process.

Dating in multiples is the perfect solution to serial monogamy since you can distract yourself from thinking  too much about one man (as women often do). This can not only help you stay objective about the men you date, but also help when one drops away – you still have another to get to know.

To wrap things up, I say yes – date them both AND keep your eyes open as you get to know them to see who has the best long-term potential, shares similar values and ways of looking at the world, is easy to be with and treats you well. If you are having fun – great! If you start noticing red flags – pay attention and don’t ignore them! And hold off on intimacy while in observation mode to remain objective. This is the best advice i can give you to guard your heart and help you make savvy dating choices on the road to finding Mr. Right.


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.

Leave a Comment