“I’m Dating an Older Guy, And He’s Not Over His Ex. What Should I Do?”

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I’m a 28-year-old woman, and I’ve been seeing a 45-year-old guy for the past two months. We have a lot in common, talk/text almost daily, and have amazing chemistry. The problem is, he was in a five year relationship that ended six months before we met, and he’s acknowledged he isn’t entirely over her and is afraid he will get hurt again. Plus, we haven’t even had sex yet even though we’ve been seeing each other for a few months. How should I handle this?

Plus: How to Dump Someone Without Being a Jerk

Your “great chemistry” and talking daily are a good start to a relationship as it provides a base to learn about your partner and grow. You’re doing just that. Paradoxically though, as the level of intimacy increases, so does the level of vulnerability. The closer he gets, the more likely he feels he could get hurt again — and fear kicks in to protect him.

How willing you are to play the role of pseudo-therapist as he grieves the loss of his past relationship while trying to build a new one?

His recent breakup likely comes with issues such as regret, anger, disappointment, insecurity, and of course fear, of which you are the object. Transitions between relationships usually aren’t seamless and often require reflection in order to grow from the experience, and to learn about what went right, what didn’t, and how to make changes to increase the likelihood of success in the next relationship. At the same time, he should recognize that just because he may have been hurt in the past it doesn’t mean he’ll be hurt again. It’s important for him to see you through a new lens.

Plus: “Sometimes I Feel Like I’m Living in the Shadow of My Girlfriend’s Late Husband.”

At this point you must decide if you want to be with him through this growth period which might include a sexless relationship. The other issue to consider is his age. The older one is the more likely he or she is to have baggage, e.g. past relationships that get in the way of new ones, messy child custody issues, and contentious relationships with ex-spouses. Your understanding, patience, and support will help him to feel more comfortable and in time connect with you sexually. However, ask yourself: how willing you are to play the role of pseudo-therapist as he grieves the loss of his past relationship while trying to build a new one? Don’t get caught taking care of someone else’s needs at the expense of your own.

Jonathan Alpert is a Manhattan psychotherapist and author.  He appears on national TV commenting on sex and relationship issues as well as lifestyle, mental health, and hot-button issues. Get more of Jonathan’s great advice in his new book, Be Fearless: Change Your Life in 28 Days.

And you can follow Jonathan on Twitter at @JonathanAlpert and on Facebook at, and visit his website at