I am Dating a Former Player and Have My Doubts On Whether Our Relationship Can Succeed Long Term: What Should I Do?

Q. I am a 31 year old woman and I have been dating a 42 year old man for the last 3 months. He has never been married and I am looking to get married soon and start a family. I have been told to be wary of any man beyond his forties who has never been married because they may likely have issues with commitment.

I asked him casually why he was never married and he said that he never felt the need to get married and when I asked him if he would ever marry, he said “Yes, I do want to get married.” When I probed into his previous relationships, he said that he was a player and had a lot of relationships with a number of women.

He is very smooth, elegant and very attractive, so that wasn’t a total surprise for me. I told him that I am looking for a long term committed relationship and didn’t want to be one more woman to his tally. He replied he wasn’t looking for a score and wanted to pursue a serious relationship.

However I wasn’t totally convinced and told him I wouldn’t have sex with him until I felt I could trust him and that for the relationship to continue he couldn’t see other women. He agreed and our relationship has grown deeper and more serious. Just recently I asked him how tough it is to wait so long without having sex and he said quite tough but he is enjoying the challenge.

Now I would like to be physically intimate with him but I am worried if he sees me as just a challenge and if he would lose interest once he sleeps with me. I wouldn’t be so worried if he wasn’t a player in the past. In terms of trust, I definitely trust him a lot more than when we were initially dating but there is just a tiny part of me that is afraid.

How do I overcome my fear and anxiety and just enjoy my time with him?

A. Dear Anxious but Interested,

I am impressed by your honesty and commitment to your goals.

You sound very sure of what you want and not afraid to put it out there. Being honest with yourself and others is always the most constructive way to proceed along life’s journey.

I understand your dilemma.

You would like certainty where there is none. Intimate relationships always contain an element of risk, because you have no control over your partner. The fact that your partner played around doesn’t rule out the possibility that he has matured out of that phase of life, and really is looking to settle down. On the other hand, he could be a life-long player who just enjoys a good challenge.

Important questions for me would address the nature of his prior relationships.

He’s never been married, but has he had any lengthy (one year or more) committed relationships in his past? Have any of his relationships been monogamous? Does he have a history of infidelity? How about in his family of origin (infidelity is often a multi-generational pattern)? What are his ideas about marriage and family? Do you think he would make a good father? Ask him his thoughts about these topics. His ability to respect your wishes about sexual relations doesn’t necessarily mean that he’ll be a good life partner.

Lastly I would say to trust your gut.

Sometimes it all looks good on paper, but something doesn’t feel right. Until it does, I would hold off on a permanent commitment. If you want to have sex with him, of course, go ahead. But if you want to reserve sex for “the one”, there’s a lot more to it than abstinence.