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Mailbag: Hooking Up With A Woman Who Has Kids Your Age

This is a recurring TFM series. Catch up with all installments of Mailbag by visiting the archive.

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Welcome to the TFM Mailbag, wherein I will answer your questions to the best of my ability. Send your questions to wescp4441@gmail.com. No topics are off limits.

Hey Wes,

I am 20 years old, and for the last couple summers I’ve been sleeping with a divorced mother who is 53. Her kids are my age, and I hate going over there when there’s the possibility that they will walk in on us, which is the most awkward situation I can think of. Lately, she has been talking about feelings and missing me. I don’t know what I should do! Do I cut and run, or play along? She is a smoke for an older woman and the sex is good, but it’s fucked how she talks about missing me and shit. What to do…? Help.

Take it easy,

Drew

Okay, so my answer to this question will be a little different than what I’d typically do.

Decent question from this guy, right? Well, what you just read is the result of some heavy editing on my part. I was going to answer the question in earnest once I fixed the numerous grammar and spelling mistakes in it, but I just have to show you guys what it was like before. So, here it is:

I am 20 years old, So the last couple summers Ive been sleeping with a divorced mother who is 53. Her kids are my age and I hate going over there then to save ourselves from the most awkward situation of the kids mother on a couch with a kid his own age. She has been talking about feelings and missing me. I don’t know what I should do? Cut and run? Or play along. She is a smoke for an older woman and good sex but its fucked how she talks about missing me and shit. What to do…? Help.

I like to think I’ve helped at least some of the people who have sent their questions to me, and that thought makes me feel a bit better about publically flogging some of you. Dissecting this fellow’s entire magnum opus might take all day, so I’m going to hone in on one “sentence” in particular:

Her kids are my age and I hate going over there then to save ourselves from the most awkward situation of the kids mother on a couch with a kid his own age.

Just how does a sentence like this come to be? My guess is that our man drunkenly slurred it through a Bane voice modulator into the text-to-speech of a broken iPhone. This is what we in the industry call a two-aspirin sentence, and it makes me tired. Not tired as in sleepy, but just tired of the world and its problems. In the moment, it makes me feel that even the greatest times I’ve yet to have, like my wedding and the birth of my first child, will somehow be tarnished by what I’ve seen here today.

Still, I’ve got to answer the question. It’s what I do, goddammit.

Okay, Drew. First off, I’m sorry your parents put you on an all-paste diet when you were little. Second, I’m going to recommend that you stop worrying about your situation. You see, things are falling right into place just as they should. Whether you like it or not, you’re the closest thing to a father figure that the kids you mentioned have in their lives right now. Everyone knows that the best way to teach teenage kids how to live is by flexing on them.

Have you ever heard “A Boy Named Sue” by Johnny Cash? Of course you have. By naming him Sue, the father manages to toughen up his kid without ever being present in his life. Your divorced lover’s children will definitely not appreciate you lighting up a post-coital cigarette on the back patio after givin’ it to their mom, but they will grow to be bitter, strong, and ready for this cruel world because of it.

Carry on, Drew. And learn to write, please.

Remember to send any and all questions you have to wescp4441@gmail.com.

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WJ Cope

He's the real reason people say "No one likes you when you're 23."

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