Falling in Love Before Divorce is Final: Should I Back Off or Can This Work Out?

Hi Evan,

Your blog has been really helpful as I find myself in an interesting situation. I’m 44, divorced with a son in college. Been divorced for a long time. Met someone at work and became friends over the course of 4 years. He’s been separated from his wife of 34 years for the past nearly 2 years. I didn’t realize he was interested in me as more than friends for at least 2 years, but I found out 2 months ago. We started dating, held off on sex until last month, but he told me last night that he came to the realization that he’s not sorted through his emotions like he thought he had.

He still wants to see me, doesn’t want to pull away, but also doesn’t want to hurt me because he’s not sure what this will entail. He’s scared, has not felt this way before, and doesn’t know what is next. The divorce will be final within the next 2 months, and I think it just really hit him, though he thought he was doing fine. We get along amazingly well, laugh together, really care about each other, and can talk to each other about anything. I’m not sure if I should step back even though he doesn’t want to, and let him work this through.

Is there a chance it can work out? I think we can have something really special together. He’s as in touch with his feelings as a man can get. I think, so hopefully, he can work through this and move on, hopefully with me. Any suggestions?


Dear Sunshine,

Ready for Lasting Love?
Ready for Lasting Love?

You’ve got to ask yourself one question: “Do I feel lucky? Well, do ya?”

Because this isn’t a matter about which I can give you a simple answer and reassurance. I understand that falling in love before the divorce is final can be scary. All we can do is look at the facts objectively, and then assess your tolerance for risk.

The good news is that you’re with an excellent communicator. He has feelings for you but has openly expressed his reservations as well. Apart from him declaring his love and devotion, you can’t ask for much more than that. Really. Lots of women say they want the truth; few of them know what to do when they receive it.

Lots of women say they want the truth; few of them know what to do when they receive it.

I know this from first-hand experience. Women always want to know what men are thinking, yet when we let you into our thought process, you immediately find fault — basically because we think things that you wouldn’t want to hear. That’s why we usually don’t say them.

“Yes, I’m attracted to other women.”

“No, I’m not positive humans are biologically programmed for monogamy.”

“Yes, I’m having reasonable doubts about whether we’re meant to be as a couple.”

These are perfectly fair thoughts that men usually don’t express in order to protect you. Then again, just because we have a thought doesn’t mean that we don’t have equally contradictory thoughts.

“I’m very attracted to you.”

“I do see the benefits of monogamy, especially in raising a close nuclear family.”


“I may be having doubts, but I’ve yet to find another partner who makes me as happy as you.”

Clearly, I have some experience in such situations, and, as always, my wife is the exception to the rule. She had been burned before by a cheating husband. And all she ever asked was to know exactly where she stood — even when it wasn’t what she wanted to hear. So when  I openly expressed my reservations that I wasn’t “feeling what I thought I should be feeling”…she didn’t panic. She took it in and let me process it. I proposed to her two weeks later and am EXTREMELY happy that I did.

To bring it back to you, Sunshine, your guy is a divorced man falling in love again. He is in a position that millions of divorcees confront as they’re getting back out into the dating scene. He likes you. He’s attracted to you. He desires a long-term relationship…but just doesn’t know if he’s ready to dive in again to a brand new life. He’s lonely. He’s made mistakes before. He wants to look before he leaps. But he just can’t help himself when he’s around you.

As such, he’s genuinely conflicted. And that’s the hardest part to deal with when you’re not conflicted. Because you have clarity, you think it should be equally obvious that he should want to embark on this new relationship. Alas, it’s not so simple.

Because you have clarity, you think it should be equally obvious for your partner. Alas, it’s not so simple.

Be thankful that you have a man who respects you enough to speak his mind, be cautious that his reservations are legitimate, and be respectful of the fact that his process might be trickier than your process.

All I can say is that I guarantee that you will definitely not fall in love if you cut him off out of fear. You at least have a chance at falling in love if you let him come to his own conclusions.

At least that’s what my wife thinks.