His Ex-Wife’s Little Sister Asked Him To Go Out On A Date, But He’s Worried It’s Weird To Say Yes

BGStock72 - stock.adobe.com - illustrative purposes only, not the actual people
BGStock72 - stock.adobe.com - illustrative purposes only, not the actual people

Nothing dramatic or colorful caused this 28-year-old man and his 28-year-old ex-wife to get divorced three years ago; it really came down to getting married way too young and realizing it years after the fact.

Their split was agreeable, and they both wound up moving away. A year ago, he returned to their hometown, and he hasn’t been privy to what his ex-wife is doing these days.

A few days ago, he ran into his ex-wife’s little sister, Riley, in the grocery store. He always got along excellently with his ex’s family, but he never knew Riley that well.

Riley is four years younger than they are, so he only really met her on a handful of occasions, and his ex wasn’t that close to Riley because of their age gap.

While chit-chatting with Riley, she revealed his ex is engaged and super happy with her new man, which he was excited about.

Riley said her parents even had asked if anyone knew how he was doing, and that made him smile.

The conversation was lovely. Before he and Riley parted ways, she actually asked him to grab drinks with her.

He figured she was being friendly, but Riley followed up by saying she understood if he didn’t want to go out on an official date with his ex’s sister.

“So it’s a date… I did end up exchanging numbers with her, asking her kind of lightly how her parents would feel, and got a “They would probably be happy that I found someone they liked,” he explained.

BGStock72 – stock.adobe.com – illustrative purposes only, not the actual people

“I figured I would rather have the number and not use it than wonder if I should have gotten it…I don’t know. I guess I was also just happy that an attractive woman asked me for my number.”

“She did mention in our conversation, before she asked me out, that she was always surprised that her sister let such a good guy go, which I corrected her and told her it was definitely mutual, not all on my ex.”

Riley is gorgeous and he had a great time catching up with her in the grocery store. He even adores her family.

If she was just a random woman, he would be over the moon about a date with her, but he keeps worrying it’s weird.

Although Riley is an adult now, she was a teen when he began dating his ex. Also, he would feel super strange to see Riley’s parents again and have them think he’s giving their second daughter a chance.

He’s concerned about what his ex will think, too, when she finds out he said yes to a date with Riley and whether or not that will strain their relationship as sisters.

“And if we got serious, I’d have to see my ex-wife at functions, which I don’t care that much about, but it’s still odd, you know?” he wondered.

“Then I got these intrusive thoughts like – is this my unconscious trying to make my failed marriage seem like a success? Then there’s like -what if Riley had the same tendencies that made you and ex incompatible? But I feel like I’m also not being fair to Riley.”

“Riley has a great family; she seems to have her stuff together, [and] she was enjoyable to talk to. I feel like I could be allowing my past to throw away a potentially great partner…I don’t know; I’m really confused. Help me!”

Do you think he should give Riley a shot, or is that opening up a can of worms?

You can read the original post on Reddit here.

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