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Woman Shares Story About Dating An Older Man While Her Sister Dated His Dumb Son (30 Tweets)

A woman posting under the handle @wetmascara on Twitter, who writes in her bio that her name is Emma, has gone viral for her absolutely wild story of dating an older man in his mid-forties at the same time as her slightly younger sister dated his 25-year-old son.

It started off with one throwaway tweet, in which she wrote, “The Thanksgiving I was 37, I was dating a 45-year-old guy, and my sister (who was 33) was dating the 25-year-old son of the guy I was dating. Partway through Thanksgiving dinner, my dad got up, went outside and mowed my sister’s yard to calm himself down.”

That is almost enough of a snapshot of the situation for me. It’s like a perfect little glimpse into the dysfunction and awkwardness of the whole scenario. Both dad and son are hot, and both dad and son are inappropriate dates to bring to Thanksgiving dinner. The dad clearly loves his daughters and wants better for them, but instead of losing it at the dinner table, he does some light yard work.  The end.

But people wanted more and Emma was happy to give it to them. She added detail after detail about why the older guy was a bad boyfriend and why the younger boy was a sweet himbo who didn’t realize his 33-year-old girlfriend was not completely dedicated to him. 

She shared how her 45-year-old boyfriend wouldn’t even commit to coming to dinner because he’s “not a planner.”

And then he dumped her soon after the whole night at her own dad’s house:


But she still had fond memories of his son:


And funny memories of the break up:


And there were some elements of farce:

What I like about the story is that if you’ve managed to live long enough you’ve been both the person dating someone too old for them and someone too young for them. Some people may love Emma’s story for the gossipy details, but I think most of us love it for the memories it brings back. Ah, to be young and stupid again instead of old and with someone young and stupid.

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