Dating & Marriage

Should I date my long-time friend who is twice divorced?

I’ve known Mr X for nearly 20 years and have seen him through two failed marriages. He is now a single parent with a young daughter, who I’m very close to. In our younger days, Mr X had expressed an interest in me but I made it clear that I was not keen in a romantic relationship with him; he respected my decision and so we remained platonic friends. Recently, his daughter asked if I can be her mummy, causing me to question my feelings for Mr X. We’ve matured together and have a comfortable relationship and I could see myself with him now, seeing this is a different kind of love and season. Should I talk to Mr X or keep my distance?


At The Well

Benny says

Dear Friendzoner,

The story that leads to your question is such a lovely one. It speaks of second chances. Your long-time friend, a single parent, has a daughter who wants to call you her mother. Though you initially had no interest to take the relationship further, you are now open to this after so many years and wonder if it may now be possible.

There are two things I have observed that goes in favour of pursuing this relationship. Firstly, you obviously know your friend rather well. For twenty years you have observed him enter and exit two marriages. With this vast stock of insight, would he make for you a good spouse and you, his good partner? Secondly, you have a strong rapport with his daughter. This is important if you are considering becoming the girl’s future stepmother.

However, here are two cautionary observations. Firstly, what do the two marital failures say about your friend: What lessons did he learn from them? Would these make him even more hesitant to enter a third marriage? Secondly, why have your feelings for him changed now? Just because his daughter wants a mother is not sufficient reason for a marriage.

As you ponder this matter from an emotional perspective, remember there are the spiritual and community viewpoints as well. Because there are various positions held by churches on marriage to a divorcee, it calls for a pastoral conversation with a minister. Also, the community of relatives and friends may want to weigh in with their views. Marriage is never only about two individuals.

Having considered all these views, if you do still have romantic feelings for him and can picture a future together as man and wife, then speak to him. Do consider working with a counsellor to help prepare you both and his daughter for any new union.