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DEAR MIDLIFE BACHELOR: I have been seeing a man for about a month. He is married (separated) and his divorce will be final very soon. We haven’t slept together yet but I want to. So my question is – do you think this is wise? I’ve been reading all the stuff about “rebound relationships”
and I don’t want to just be a temporary balm and sex outlet while he is still recovering from his failed marriage. Conventional wisdom suggests I will be the one who gets hurt down the road. On the one hand, part of me wants to just go with it, regardless of the outcome. This could possibly be because it has been a VERY LONG TIME since I’ve been with anyone and the floodgates have opened, if you know what I mean. On the other hand, I’m fairly sure I’ll take it hard later on IF this turns out to be a bona fide go-nowhere rebound relationship. Do you think I should just assume this from the get-go and enter into it physically with my eyes open, or just play it safe and end it right now? I do find him intriguing although it’s way too soon to know if there’s long-term potential. What would you suggest?

  First, on the subject of being “on the rebound”, there is a good discussion on that topic from a man’s point-of-view here on, called Rebound – Does Fear of Being Single Drive Your Behavior?  Reading that page may give you some ideas of what to look for in terms of “rebound behavior” by this man.

He may or may not be “on the rebound” – it is hard to say based on what you state above … not really enough information. Regardless, in terms of what I’d suggest that YOU do or consider is this – one motto of is ALWAYS GO FOR IT … which really can mean either “push the envelope of the situation” or in its most extreme case, it means definitely have sex. Part of the reason for the existence of that slogan is that you never really know what is coming next … and if you don’t TRY to push that envelope, then you risk the envelope not ever getting pushed. An interpretation of that in your exact situation is – you have nothing to lose by sleeping with him now … except MAYBE a broken heart later on … but MAYBE your heart would be broken later on REGARDLESS of whether you sleep with him now or not. So since you say that it has been a long time for you AND the “floodgates are open” (your words) – I’d suggest that you go for it, and give it your all … have sex with him … you have nothing to lose.

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.