Am I wrong for rejecting a woman who once rejected me?

Years ago, a young man’s heart skipped a beat for Nat, a friend who laughed off his date request with a polite but stinging rejection. Fast forward, and this Reddit user, now confident and thriving, finds himself back in his hometown, crossing paths with Nat again.

But when she flips the script, pressing him to rekindle what never was, his firm “no” unleashes a storm of texts from her friends. Now, he’s brewing a coffee meetup to squash the drama—will it clear the air or stir more chaos?

‘Am I wrong for rejecting a woman who once rejected me?’

I (Male, mid-twenties) spent most of my childhood and early adulthood focused on education. I'm not naturally gifted, so I had to focus and work hard, as my parents encouraged me to. Things finally slowed down later during college, and I found myself being more social. There was a girl, Nat, in my social circle whom I liked so I asked her out.

She laughed when I did, but she said it was just so unexpected and that's why she laughed. Still, it kinda stung. She declined and said she wasn't dating at the moment. Spoiler alert: she was definitely dating, just not me. But whatever, she said no, I moved on. I got a good job out of my hometown, partly based on my good school performance and connections through internship.

Two of the guys from work, let's call them Tony and Steve (mid to late thirties), hung out with me a lot and got me to come out of my shell more. They told me to start coming to the gym with them cuz they were

Now, Tony and Steve were a couple, so whenever we would go out, they'd be really good wingmen and really got me out of my shell. I'm still a bit awkward, but much more comfortable in social situations now that I've got some experience. This happened over the course of like, two years.

I wound up asking my job to work remotely to be closer to my family (health/money issues back home, not going to get into it), and got approved as long as I travel back to the office quarterly for important meetings and stuff. So now I'm back home, again. I ran into Nat at the grocery store a few weeks ago.

Turns out, she's raising a kid on her own now and generally doing well for herself. We ran into each other again at a mutual friends' party. This is when she asked when I was gonna ask her out again. I said the thought hadn't really crossed my mind and she seemed offended like, why not. I said I'm not interested and thought that was that.

I did kinda remove myself from the conversation quickly after that. Well, apparently that wasn't ok to do. Nat came and found me again and demanded to know why I'm not interested because

She said a normal person would be over that and then said it's because she's a single mom, isn't it? I mean, honestly, I've no interest in dating single mothers because I'm literally just now dating around. I don't want to have to deal with all the stuff that comes with a situation like that. But more to the point: I'm not attracted to Nat anymore. I just simply don't see her that way.

Am I crazy here? Like, why are her friends blowing me up because I don't want to date her? Tony and Steve are telling me that I don't owe her anything, but some of my friends at home are telling me to at least give her a shot. I haven't really talked to my parents about it, but my younger brother is saying I should try and my older sister is telling me to trust my gut. I just don't understand why or how this got to be such a big deal.

UPDATE: After reading and replying to some of the overwhelming amount of comments here, I spoke with my sister last night about what to do. I don't like the chaos of this situation, it's a lot of anxiety and I feel the need to resolve it. To that end, after much consideration and my sister's agreement, I reached out to Nat this morning and asked her if she would meet me for coffee tonight.

I made it clear that this is NOT a date, it's just two friends trying to come to terms with each other because I don't like all the messages and comments from her friends. Nat accepted pretty quickly and said she'd like to clear the air about some things. The fact that she apologized for

The OP’s dropped an update on the saga—curious? Click here to check it out!

Navigating past rejections can feel like walking through a social minefield, especially when old flames resurface with new expectations. The Reddit user’s decision to reject Nat reflects a healthy focus on his own growth and preferences. Dr. Susan Krauss Whitbourne, a psychology professor, notes, “Personal boundaries in relationships are crucial for maintaining self-respect, especially when past interactions left emotional scars” (Psychology Today). His choice to move on, despite Nat’s insistence, shows emotional maturity.

Nat’s reaction—demanding explanations and rallying friends—suggests insecurity, possibly amplified by her current life as a single mother. The user’s discomfort with dating single parents is a valid preference, not a judgment on Nat’s worth. A 2024 survey found 59% of young adults prioritize personal compatibility over societal expectations in dating (Pew Research). Nat’s past lie about not dating adds context to his distrust, making her pushiness a red flag.

The broader issue? Social pressure can blur personal boundaries, especially when others project their desires onto someone’s choices. The coffee meeting is a constructive step, but he should stay firm on his stance. Advice: Keep the conversation civil, clarify intentions, and disengage if drama persists.

See what others had to share with OP:

Reddit threw their hats in the ring for this rejection saga—grab a snack for these spicy takes:

[Reddit User] − Bro listen to your gay friends. Tony and Steve seem like people who actually care about your happiness.. Good Bros are hard to come by. You guys listen to your homies, homie.

Jsmith2127 − You saying that you are not interested is enough. Its pretty pathetic that she is now harassing you, and having other people harass you just because you don't want to date her... that would make me be more turned off towards her. Does she think arguing with you, about why you won't date her, and getting other people to message you over it would make you what want her more, or guilt you into dating her?

Magdovus − Given that she laughed at you last time why should you give her a chance now?

Grimnar49 − This sounds like her problem not yours. You got rejected and improved yourself for your own confidence and mental health. She bumps into you later probably regrets not accepting 2 years ago after seeing how you changed and is lashing out because you’re no longer interested.. You’ve dodged a bullet by the sounds of it.

No-Mango8923 − Listen to you sister. She's right. Nat just wants a surrogate baby-daddy, and you're her only hope now that no one else wants a single mom in her situation.. Stick with your gut instinct and avoid her like the plague.. She said a normal person would be over that. Tell her that is exactly how you feel about her - you're over her like any normal person would be after 2 years :)

According_Stuff_8152 − You should have told her you were not dating anyone at this time.

CosmeticBrainSurgery −

And this was all after lying to you and laughing at you, which I gather she never apologized for, because she doesn't think you're valuable enough a person to take exception to shoddy treatment. She's spoiled and emotionally abusive.. You dodged a bullet, my friend.

Darthkhydaeus − No way. There is literally no benefit to you dating a single mom as a guy with options, let alone one who was not interested when you were less successful.

[Reddit User] − Steer clear of her. Any woman who first turns you down (and lies that she isn't seeing anyone). Then, when you muscle up and learn to be social and have a good job, you're dating and maybe marrying material. She dislikes you're doing what she did or what I say, I can ghost you, but you may NOT ghost me!

If you ever decided to date her, she will always feel she is doing you a big favor and let you know any chance she gets. To repeat, look elsewhere as she is bad news. That's not adding she's a single mom, something you say you don't want to deal with. Not even as friends as she will keep trying to become your girlfriend and may think she is when she isn't.

evil_overlord01 − Bro, you leveled up & she now has limited options. Might be harsh, but it's the truth. Trust your gut & stay away from her. Don't fall victim to the pressure from anyone.

These Reddit roasts are hot, but do they cut through the noise or fan the flames? One thing’s clear: this drama’s got everyone picking sides.

This Reddit user’s journey from rejection to confidence shows the power of trusting your gut, even when old crushes come knocking. His coffee plan aims to douse the drama, but Nat’s pushy vibe raises eyebrows. Have you ever had to shut down a past flame who wouldn’t take no for an answer? Drop your stories below—what would you do in this caffeinated showdown?

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