I’ve been seeing a really great guy for about 3 months, and it feel really right. We spend a lot of time together and include each other in our plans. I am 37, and he’s 42. He says he wants to get married and have children (these are things I want), but that he’s worried that he is too old and that it doesn’t seem likely to happen for him. Meanwhile, he also tells me that he loves being with me and looks at me lovingly. Am I overlooking a big red flag? Or, is this just nothing and he means what he says (that he wants kids and a wife)? Thank you for any insight you can provide.


First, read this article, called “Believe the Negatives, Ignore the Positives.”

I’ll wait.

Next, your question begets a few more questions.

Ready for Lasting Love?
Ready for Lasting Love?

First, the guy you’re “seeing” – is he your boyfriend? You may feel weird about the title, but the title matters. A boyfriend has the potential to turn into a fiancé. The guy you’re seeing for three months who has not claimed the mantle of boyfriend is not a good bet.

Boyfriends act like this, by the way.

Next, I appreciate you reaching out to me for my interpretation of events, but you know who would be the best person to tell you what this guy really means? This guy!

Stick with me, because I know this sounds crazy, but when you have a question about some intentions, the only person who can REALLY know what he’s thinking is HIM.

You’re not trying to trap him. You’re not trying to interrogate him. You’re not trying to force him into a premature proposal or promise ring.

Dump the “I don’t know if I want a family” guy.

You’re trying to clarify a statement that didn’t add up in your head:

“You’re 42, you want a wife and kids, you have a girlfriend who wants to get married and start a family – why would you say that it’s not likely to happen?”

See how he answers.


Perhaps, he will fumble his reply and reveal that he’s actually ambivalent about those things (which is your cue to leave!)

Or, more likely than not, he’ll tell you that he would like to believe it’ll happen for him, but after years of mistakes, rejections and regret, it’s hard to feel optimistic about any new relationship.

How do I know this?

Because it’s the exact same thing that women have been telling me for years when asked about starting a family in their late thirties/early forties.

Forgive the insecure guy. Dump the “I don’t know if I want a family” guy.

Life is too short to wait to see if he figures it out on your watch.