We have a 25-year age gap. 13 years ago, our relationship didn’t work. But could now be our time?

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Amy & T.J.,

When I was a freshman in college, I fell in love with a man 25 years older than me. The connection was unshakable, but I was young and he was newly divorced, co-parenting eight kids. It didn’t work.

It’s been 13 years, I’m about to turn 40 and he’s stepped back into my life. I think we’ve both grown a lot and might be ready for a real relationship. He worries that my parents and friends won’t approve, but I don’t want to crowdsource my relationship.

If we try again, will it be the same old story? Or could it be for real this time?

— Casi

Gut reaction

T.J. Holmes: You technically could’ve been one of the children. If we heard their two ages today, we wouldn’t necessarily raise eyebrows. So what is the danger of exploring something you thought you had with a guy all those years ago? Still, if you were a friend of mine or family, I would give you a number of cautions.

Amy Robach: I will say, now that his children have most likely grown up and gone on to live their own lives, they’ll be less of an issue. So I think your relationship would have a much better chance at success today.

On further thought…

TJH: I do raise an eyebrow at your history. I wonder what the relationship dynamic between you and this man would have been like when you were a freshman in college. What real history do you have? I don’t think it’s impossible that there was a genuine connection, but there’s a maturity gap there. A guy with eight kids has done a lot in his life, and a freshman in college hasn’t. It’s hard to understand how that would have worked.

AR: I can certainly understand why it didn’t work then, but I’m going to take the positive approach now. I would tell you to go for it. What do you have to lose if you really feel like you have a connection with this man? You’ve now been apart from one another for 13 years, and you’ve been able to experience life separately and grow and mature — especially you, but maybe him too, because honestly, some 40- and 50-something men aren’t that mature.

TJH: This is what you’d tell your own daughter?

AR: I would say to date with caution, even with cynicism. You need to really think about all the things you want in life. Among them: Do you want children? Does he want more children? Those are important conversations to have when you’re dating someone with that big of an age gap, especially someone who has that many children already.

But with those questions in mind, why not give it a try?

TJH: My advice to you, as a stranger, is: Go explore, why not see what happens?

But if you were my daughter, I would say none of the things I just said.

If I were talking to my own daughter, I would say: “Are you out of your freaking mind? You shouldn’t have anything to do with him.” We would need to have a conversation over dinner tonight about what was going on when you were a freshman in college. As for wondering if he wants kids? You could be one of his kids. You’re a grown woman, do what you want to do, but if you were my daughter, I’d be asking you not to do this.

AR: I have to wonder how you met him when you were a freshman in college and he was 25 years older. Was he a professor? Because when someone you meet is an authority figure and older, that creates all sorts of issues. It’s less about the age difference and more about the power and experience difference. If you decide to try it again now, more than 10 years later, is that dynamic still going to exist? Probably. Are you coming together as equals? There’s still an experience gap.

TJH: But it worked for French President Mr. Emmanuel Macron and his wife.

AR: But they had that fight!

The final word: Does family opinion matter?

TJH: As for not wanting to “crowdsource” your relationship decisions? Take the word out of your vocabulary. You’re not “crowdsourcing” a decision; you’re doing what a smart person does before making a major choice: getting counsel.

AR: Trust the people who love you the most. I always tell my daughters, “No one loves you more than I do.” No one wants the best for them more than I do. I don’t always know what the right thing to do is, but I know I’ll have their best interests at heart. You have people in your life who love you — lean on them.