Welcome to of our new advice column where we try to answer all of your confounding “What The…?” questions. We’ll be getting advice from experts, but we may not always have the best answer. Feel free to share your own advice in the comments below .
I really like this man and would like to date him seriously. We’ve been friends for a long time — decades in fact, but he was married and therefore off-limits. Not anymore! Everyone tells me not to be his first post-divorce girlfriend because it won’t last. Myth? Truth?
Rebound or Romance?
Upon dissolution of his relationship, the long-married man could behave in a variety of different ways. Some go completely apeshit-horndog, sliding their penis into any and all willing receptacles. After decades of mundane marital life, they can’t believe they’re suddenly in demand. They see vagina around every corner. They are the binge-eater at the buffet, gorging themselves on an abundance of boobies and beav at their collective fingertips. After all, these once longtime married guys (usually) haven’t had the chance to go feral, unlike some of their single brethren (who are still sleeping on futons and getting the band back together for one last gig at the Paramus Fuddruckers). These are the dudes your friends are warning you away from.
But then there are the types who don’t really know how to be single. They’ve been married so long that they no longer know how to flirt. The idea of online dating confounds them and they have absolutely no idea where one purchases new underpants. Any sex act that’s not the missionary position is taboo and kinky, which can make them very gratifying sex partners.
Predictably, these types are not without issues either. For one thing, after 20-plus years of not really having to impress anyone, they know very little about courtship. They tend to be insta-relationshippers and will be shocked that you expect a little wooing and aren’t prepared to cook Thanksgiving for his extended family.
Then again, maybe he’s just over his marriage, and ready to start the next phase of his life with an old-pal-turned-new-luvuh-lady by his side. Life is full of little risks and this seems like one worth taking.
One thing you don’t mention in your letter is whether or not your buddy has expressed any interest in taking your friendship in a less clothed direction. I would sound him out on that first and proceed with caution. But yes, proceed. Life’s too short not to occasionally wad conventional wisdom up into a ball and toss it in the dumper.
This website is provided for informational purposes only. Always discuss topics like this with a trained professional or a best girlfriend.
Have a Burning Question?
Write to us at firstname.lastname@example.org with the subject line “Ask TueNight”