I (28m) ran into my ex wife’s sister (24f) at the store. After catching up she asked me on a date. I have mixed feelings. What should I do?

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Imagine strolling through the grocery store, minding your own business, when a familiar face sparks a conversation that takes an unexpected turn. For one 28-year-old man, a chance encounter with his ex-wife’s younger sister, Riley, turned a routine shopping trip into a whirlwind of emotions. Three years after an amicable divorce, her bold invitation for a drink—clearly a date—left him torn between flattery and unease, wondering if saying yes would open a can of worms.

The past lingers like an uninvited guest in this tale of new possibilities. Riley’s charm and their easy chat hint at a fresh start, but the shadow of his ex-wife and her family looms large. Readers can’t help but ponder: is this a recipe for romance or a shortcut to family drama? The stakes feel high, and the decision isn’t as simple as grabbing a coffee.

‘I (28m) ran into my ex wife’s sister (24f) at the store. After catching up she asked me on a date. I have mixed feelings. What should I do?’

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. Quick background, my ex wife is the same age as me, and I have not seen her since we divorced three years ago.

There was nothing juicy about the divorce, just two kids who got married too young, too soon, and realized it too late. We divorced pretty amicably and she ended up moving away. I did as well for a time, but I ended up coming back home last year, I had no idea what my ex was doing and didn't really care.

I got along with her family until the end, although 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.

My ex was not really close with her sister but they also did not have any ill will toward each other. Anyway, she told me that my ex is engaged and happy, which I was actually happy to hear. She said her parents are doing well and they even asked her a little while ago if she knew what I was doing, which she didn't because I don't keep in contact with anyone from her family (kind of wanted a clean break, you know?).

We (me and ex) do have some mutual friends but I don't think Riley really knows them that well. It was a nice conversation. Before we finished talking Riley asked me if I would like to have a drink with her sometime. I thought maybe she just wanted to catch up in a better setting (more so than two people leaning on shopping carts),

but then she said 'But I understand if you don't want to go on a date with your ex wife'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.'

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 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.

But I keep thinking that it's weird, like, she's obviously a grown woman now but she was a teenager when I started dating my ex wife (as I said I didn't see her all that much so no, this is not a grooming situation), 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? 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?

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, 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!

Navigating a date with an ex-wife’s sister is like walking a tightrope over a family reunion. The OP’s hesitation reflects a natural concern for boundaries and optics—after all, Riley’s invitation, while flattering, carries baggage. He’s drawn to her charm and their shared connection through her family, but fears stirring up drama or misperceptions. Riley’s confidence suggests she’s unbothered, yet her sister’s feelings and family dynamics remain wild cards.

This situation touches on broader issues of post-divorce relationships and family loyalty. A Psychology Today article notes that post-divorce interactions with ex-family members can trigger unexpected emotions, especially when new romantic ties form. The OP’s worry about awkward family gatherings or speculation about past overlaps is valid—people love to gossip.

Dr. Susan Krauss Whitbourne, quoted in Psychology Today, advises, “Divorce doesn’t end relationships; it redefines them.” For the OP, this means proceeding with caution but not ruling out a connection. He should first clarify Riley’s intentions and discuss potential fallout, like her sister’s reaction. A casual coffee, not a full-on date, could test the waters without committing.

Check out how the community responded:

The Reddit squad didn’t mince words, dishing out a fiery blend of warnings and shade. From cries of “drama alert” to tales of sibling rivalries gone wrong, they’ve got opinions hotter than a summer barbecue. Here’s the raw take from the crowd:

PermaThrowaway111 − 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.

Artneedsmorefloof − Serious questions to think about -. If your ex-wife was dating/marrying your brother/best friend, how would you feel about it?. If your best friends' ex asked you on a date, how would you feel about it? If you went out with your ex's sister, are you prepared for speculation that you and her had something going on while you were married to your ex?

(Not saying you did, but people being people someone is going to bring it up). -- Seriously though - while you don't have children - that is a weedy snake-filled pool to wade into for both of you. You are both consenting adults so do what you want but make sure you understand you are not going into a situation that everyone is going to be supportive and happy about.

jackjackj8ck − Dude…. # NO

helendestroy − (they also always liked me). That would not be the case this time round. FFS.

Cultural_Shape3518 − There are literally billions of women out there.  I have to think there’s at least one decent match for you that doesn’t happen to be related to your ex-wife.

SuspiciousSlip7604 − As a younger sister I can’t fathom the idea of going on a date with my siblings ex bf’s, let alone ex husbands. Not only have you shared very intimate moments together, physically and emotionally. You said vows to each other, had a whole ass wedding.. I’m not sure what revenge plot this younger sister is on, but stay far away from it dude.

Choice-Intention-926 − It’s going to be awkward. Especially if she doesn’t get the ok from her sister first. Every single family get together will be a nightmare.

jbswu − You know d\*mn well this is a terrible idea, and she's absolutely crazy for even proposing it. For the love of God, find someone that you don't have to come to Reddit asking if it's a good idea to even entertain them.

raerae1991 − Are you a drama queen? Why are you even thinking about it?

AtomicPoetry − Many moons ago, in my high school days, my older sister dated a guy who enjoyed the same video game as me. We would chat about it for hours when I saw him, but our relationship was platonic. They broke up after a while. Five years later, I met him again at a convention. He asked me out.

I declined. When I told my sister her response was, “I knew he broke up with me because he was in love with you!” That was over 25 years ago and she still mentions it at Christmas that I’m a boyfriend stealer. Today, she’s happily married and has kids.. OP, don’t do it.

These Redditors sound the alarm, urging the OP to steer clear of Riley’s invite or risk a family soap opera. Some see her move as a red flag, others just cringe at the awkwardness. But do their dire predictions hold all the truth, or are they fanning the flames of caution? One thing’s certain: this grocery store plot twist has tongues wagging.

The OP stands at a crossroads, weighing a spark of attraction against a potential family feud. Riley’s bold move could be a chance at something new or a ticket to awkward holiday dinners. What would you do if an ex’s sibling asked you out? Share your stories and advice—how do you navigate the murky waters of past and present relationships?

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