Love Letters: Should I Date A Man Who Has Been Married Twice Before?

two times

This one’s for the lovers.

Got a burning question about your love life (that isn’t a medical condition)? Hit me up.

Send your inquiries to, or find me on Twitter @etbowser. Just provide your initials, or a fun nickname. 

Here’s today’s question:

I’m a 37-year-old single young lady with no kids. Recently my friends hooked me up with a young man that’s 40 and single, no kids but he’s been married twice. Should I be gun shy? Married twice at 40 seems, well, a little shall we say suspect?

Better Safe Than Sorry

Look playas, I’m all for discretion, especially when it comes to new relationships. Some of y’all will meet someone with relationship potential on Monday and will be maxing out your credit card at David’s Bridal by Thursday.

Still, let’s not jump to conclusions here. Yes, two marriages in what we can assume is the span of 20 years seems a bit off, but that’s not an automatic condemnation of character.

I mean, it’s as short-sighted and offensive as your auntie saying to you: “You’re a 37-year-old single woman? You’re not married YET? Must be something wrong with YOU.”



Yep, she deserved those hands.

Likewise, you don’t know what this man has gone through. Those previous marriages could have been destroyed by an unfaithful spouse, sudden death – anything. It’s not NECESSARILY all his fault.

Making snap judgments are wrong but you’re absolutely right to proceed with caution – as you should with any other relationship. If you’re interested in this guy, spend some time with him. Over the course of a couple dates (NOT 10 seconds into the first date, calm down) inquire about those former marriages. Find out the real story. It might not be fair to hold his past against him if he’s come out of those failed relationships a stronger person.

And, as I always preach around here, TAKE THINGS SLOW.

Don’t crucify this guy for his past when you don’t even know his story. Who knows? Third time could be the charm.

Just don’t go rushing down the aisle, please.

One more question before we wrap up:

Why do men tend to bark up the wrong tree? Meaning why do men try to holla at women they know they don’t have a snowball’s chance in Hades with?

Out of Your League

See, I never got this mentality.

How do you define one’s “league?” Are PhDs only allowed to holla at other PhDs? Must you have matching tax brackets before you’re both allowed to hit up Outback Steakhouse?

Listen, as long as a confident, genuine brother approaches a woman respectfully (and that woman isn’t already in a relationship) I think he should give it a shot.

I mean, what’s the worst that could happen? You can’t fault a brother for trying.



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