Man Torn After Ex-Wife's Sister Randomly Asks Him on Date

An anonymous man admitted to "mixed feelings," which he detailed in a post to Reddit's Relationship Advice forum, after a surprise encounter with his ex-wife's sister led to an even bigger surprise. Now, OP (a.k.a., the "Original Poster") isn't sure what the right move is, or even what he should be feeling about what just happened. After he lays it all out for the internet, they lay into him -- definitely not unsure about how they're feeling! The man wound up coming back to his post with a couple of edits to his original post just to address the onslaught of reactions and accusations -- ("I'm not a bad person") -- while also sharing that the whole experience taught him something he hadn't realized about himself. Could it be a surprise meet-cute to tell their friends and family in the future? OP seemed truly uncertain about how he should take a chance encounter, opening his story with the background basics. "I'm a 28(m), I recently ran into my ex-wife's sister Riley (24f) at the grocery store, and after talking with her and sort of 'catching up,' she ended up asking me out on a date, and I'm not sure how I feel about it," he wrote, quickly summing up the situation. He then went on to expand that his ex-wife is his age and they've not seen one another for three years, nor has he stayed in touch with her family. "There was nothing juicy about the divorce, just two kids who got married too young, too soon, and realized it too late," he explained. OP explained that he "got along with her family until the end." As for his ex-wife's sister, OP added, "I did not know her sister that well since either we were in college or she was in college (away from us), but I obviously had met her several times and had a cordial relationship with her - never felt any weird vibes while married to her sister." He also noted his ex wasn't that close with her sister, but "they also did not have any ill will toward each other." During the catch-up, he learned his ex is engaged and happy, her parents are well and had even asked Riley how OP was doing, which she didn't know as he and his ex "kind of wanted a clean break." "It was a nice conversation," OP wrote, before adding that Riley then asked him if he'd "like to have a drink with her sometime." He thought it was a casual thing, but she then told him, "But I understand if you don't want to go on a date with your ex wife's sister." "So it's a date..." he wrote, setting up his uncertainty. They did exchange numbers and he did ask what she thought her parents would feel, "and got a 'they would probably be happy that I found someone they liked.'" OP noted, "I figured I would rather have the number and not use it than wonder if I should have gotten it...I don't know." He then went on to share some of his other thoughts about the whole thing, writing, "I guess I was also just happy that an attractive woman asked me for my number." He also noted, "Riley is very pretty, I enjoyed talking to her, and I like her family (they also always liked me)." "If I had just run into her as a stranger and there was no history, if I'm being honest it would have made my day to have been asked that," he continued, but because it was Riley, "I keep thinking it's weird, like, she's obviously a grown woman now but she was a teenager when I started dating my ex wife." He quickly dismissed potential "grooming" accusations, reiterating he "didn't see her all that much," but did add, "I would feel weird going to her parents, almost being like 'hey, I decided to give your other daughter a try!'" "Then how would my ex feel about it? Would it ruin her relationship with her sister?" he continued. "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?" "Then I got these intrusive thoughts like - is this my unconscious trying to make my failed marriage seem like a success?" OP went on. "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," he concluded his initial post. "Riley has a great family, she seems to have her stuff together, 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!" "Like... What kind of head injury makes him think this would be a chill fun time ????" commented one Redditor, while another responded rather crassly, "His d--k." Another reacted, "I’m dead at this answer because in what f--king world could this ever be a good idea ???? guy is living in a rom com in his head." Another commenter offered a similar response that got OP's attention, writing, "Politely decline, because this is a chaotic mess in the making. Don't think with your d--k, chief." OP wrote back, "I really didn't think that

Man Torn After Ex-Wife's Sister Randomly Asks Him on Date

A man turns to the internet with "mixed feelings" after a random run-in with his ex-wife's sister escalates from "catching up" to being asked out on a date -- and suddenly has to defend himself from online accusations he's "thinking with his d--k."

An anonymous man admitted to "mixed feelings," which he detailed in a post to Reddit's Relationship Advice forum, after a surprise encounter with his ex-wife's sister led to an even bigger surprise.

Now, OP (a.k.a., the "Original Poster") isn't sure what the right move is, or even what he should be feeling about what just happened. After he lays it all out for the internet, they lay into him -- definitely not unsure about how they're feeling!

The man wound up coming back to his post with a couple of edits to his original post just to address the onslaught of reactions and accusations -- ("I'm not a bad person") -- while also sharing that the whole experience taught him something he hadn't realized about himself.

Chance Encounter

Could it be a surprise meet-cute to tell their friends and family in the future? OP seemed truly uncertain about how he should take a chance encounter, opening his story with the background basics.

"I'm a 28(m), I recently ran into my ex-wife's sister Riley (24f) at the grocery store, and after talking with her and sort of 'catching up,' she ended up asking me out on a date, and I'm not sure how I feel about it," he wrote, quickly summing up the situation.

He then went on to expand that his ex-wife is his age and they've not seen one another for three years, nor has he stayed in touch with her family. "There was nothing juicy about the divorce, just two kids who got married too young, too soon, and realized it too late," he explained.

OP explained that he "got along with her family until the end." As for his ex-wife's sister, OP added, "I did not know her sister that well since either we were in college or she was in college (away from us), but I obviously had met her several times and had a cordial relationship with her - never felt any weird vibes while married to her sister." He also noted his ex wasn't that close with her sister, but "they also did not have any ill will toward each other."

During the catch-up, he learned his ex is engaged and happy, her parents are well and had even asked Riley how OP was doing, which she didn't know as he and his ex "kind of wanted a clean break."

"If I had just run into her as a stranger and there was no history, if I'm being honest it would have made my day to have been asked that"

"It was a nice conversation," OP wrote, before adding that Riley then asked him if he'd "like to have a drink with her sometime." He thought it was a casual thing, but she then told him, "But I understand if you don't want to go on a date with your ex wife's sister."

"So it's a date..." he wrote, setting up his uncertainty. They did exchange numbers and he did ask what she thought her parents would feel, "and got a 'they would probably be happy that I found someone they liked.'"

OP noted, "I figured I would rather have the number and not use it than wonder if I should have gotten it...I don't know."

He then went on to share some of his other thoughts about the whole thing, writing, "I guess I was also just happy that an attractive woman asked me for my number." He also noted, "Riley is very pretty, I enjoyed talking to her, and I like her family (they also always liked me)."

"If I had just run into her as a stranger and there was no history, if I'm being honest it would have made my day to have been asked that," he continued, but because it was Riley, "I keep thinking it's weird, like, she's obviously a grown woman now but she was a teenager when I started dating my ex wife."

He quickly dismissed potential "grooming" accusations, reiterating he "didn't see her all that much," but did add, "I would feel weird going to her parents, almost being like 'hey, I decided to give your other daughter a try!'"

"Then how would my ex feel about it? Would it ruin her relationship with her sister?" he continued. "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?"

"Then I got these intrusive thoughts like - is this my unconscious trying to make my failed marriage seem like a success?" OP went on. "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," he concluded his initial post. "Riley has a great family, she seems to have her stuff together, 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!"

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Reddit Unloads

"Like... What kind of head injury makes him think this would be a chill fun time ????" commented one Redditor, while another responded rather crassly, "His d--k." Another reacted, "I’m dead at this answer because in what f--king world could this ever be a good idea ???? guy is living in a rom com in his head."

Another commenter offered a similar response that got OP's attention, writing, "Politely decline, because this is a chaotic mess in the making. Don't think with your d--k, chief." OP wrote back, "I really didn't think that's what I was doing but man, the more I read these replies..."

"His d--k is trying to f--k the whole family. Who's next, the mom?" asked another commenter. "Man needs to be realistic. If he gets with the younger daughter, there will be definite suspicions that he groomed her or something as a teenager."

"His d--k is trying to f--k the whole family. Who's next, the mom?"

The onslaught was pretty relentless, and not at all supportive of OP even considering such a thing.

"I think you'd have a better time being waterboarded than having to attend family functions where you're dating your ex-wife's sister," offered another in the top-voted comment, with more than 4.5K upvotes.

While many were tearing into OP for even considering this, there was some appreciation for the complexity and honesty of his thought processes. "I'm impressed by OP's honesty and ability to own his feelings and 'stuff,'" wrote one. They even suggested that after some counseling and a chat with the ex, he could "re-address the possibility."

OP was very active in the comments, like when asked about possible future comparisons, he admitted he hadn't thought that far. "A couple people mentioned things like if I 'saw her naked and she looked like her sister how would you feel?' - I didn't even freaking consider that," OP wrote. "One that actually grossed me out - 'Am I better than my sister,' - seriously, I had not even considered that."

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A lot of people called the sister out, suspicious of her intentions. While some conceded maybe she'd just heard great things about him, others saw another possibility. "The younger sister is a snake," wrote one, while another warned, "I’m not sure what revenge plot this younger sister is on, but stay far away from it dude."

Calling the sister "messed up" for even asking him out, one Redditor wrote, "I am going to say it straight out, don't do it! That would not only be disrespectful and hurtful to your ex, you would be opening the door to so much drama and mess. So if you care about your ex at all anymore, you will not do this to her."

Another agreed, commenting, "There are 3-4 billion other human women in the world. Pick someone whose family won't find you banging them extremely awkward."

"Is she the only woman in your 100 mile radius?" asked still another.

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Self-Realization

As it went along, OP began to realize that a lot of his uncertainty in this situation -- which Reddit seemed to have zero uncertainty about -- was more about where he was at in his life than the sister or her offer of a date.

"I think I initially did not want to admit - or even realized - how much of this is the fact that I really miss having a woman who loves me and who I can love," he wrote in one comment. "I think the fact that it was my ex's sister really opened up a chest in my brain that was previously under lock and key."

One Redditor simply declared, "This is hands down the dumbest post I've read on her in a while." By this point, OP had decided what they were going to do and seemed in much lighter spirits, replying, "Well, at least I can claim a milestone."

On his way to more than 100 replies to comments, OP jumped into his original post twice with some Edits/Updates. These were to address the mostly brutal reaction he got online -- which he truly didn't seem to expect -- as well as update how he responded to his ex-wife's sister.

"Call me dumb, naive, oblivious, emotionally unintelligent, etc. - but I'm not a bad person and I never intended to destroy anyone's relationships"

"I have read through your comments, taking my lashings from some, gotten some weird, creepy personal messages from others who as one person put it, understood why I wanted to "knock boots" with my ex's sister," he wrote, crediting more the "creepy 'pro' messages" than those telling him not to go through with the date for his final decision.

"I texted Riley and told her that I don't think it is appropriate for us to go on a date. I told her that I enjoyed talking to her and catching up but that we should only be cordial if we see each other out but nothing more," he wrote. "Maybe I shouldn't have said this but I also told her that it is nothing personal against her, that she seems like a really great person, but given my history with her sister it just isn't appropriate."

OP wrote that Riley "understood and respected" his decision, but didn't think his ex-wife would have an issue. Nevertheless, he stood strong, telling Reddit he "also learned a lot about myself here."

While the 100+ comments showed him coming to these realizations in real time, he summed up, "I miss being a husband. I miss being in a loving marriage. I don't miss my ex wife, but I miss what we once had and I want that again (with someone else). I didn't know I felt that way, at least consciously, until I spoke to Riley."

While he has dated since his marriage ended, OP suspects that because they shared no connections to his marriage, "I could still repress those feelings." He wrote, "didn't realize how lonely I was and how much I craved having a woman that I could come home to and not just receive love, but give it."

"Finally - call me dumb, naive, oblivious, emotionally unintelligent, etc. - but I'm not a bad person and I never intended to destroy anyone's relationships," OP concluded his update. "I also was not thinking about sex (thinking with my d--k)," admitting he hadn't even considered much of what Redditors brought up.

"I was thinking with a heart that confused scar tissue with being healed. As for Riley, I don't know what her intentions were, and at this point I don't care," he continued. "I am not going on that date with her, I'm going to talk to a professional about my unresolved love issues, and I want to thank everyone here for opening up my eyes, even if you were a jerk - except the person who basically accused me of being a p*do - you can f--k off."

What do you think?