I feel guilty for letting him pay. Should I dm him to pay him back after 5 years? 😭?

[Zoeyyyyy]

I know this situation might be weird but:
About 5 years ago I went on a date with this guy, he was very sweet. He insisted to pay the bill after I multiple times said to split. He still paid (about $90)
So I said to him: thank you, next date I’m paying. Which I genuinely wanted to. When I came home and I’ve got to think about it in peace he just didn’t feel right to me and when he texted to plan a 2nd date I really felt like I didn’t want to go so I made up an excuse and we never talked after that. It’s been 5 years and he is in a happy relationship with a different girl and so am I with my partner. After all these years I still feel guilty about letting him pay and not giving anything in return. Is it weird if I would DM him after 5 years to apologize and that I want to send him the money for my part of the bill?

[ChicoFromThe305]

No don't overthink it, he was happy to pay and you offered on the spot which you did what you felt was right, the only times men aren't okay with paying the bill is when women feel entitled that it's a must that a guy should do it for them, you've shown a humble side he most likely appreciated and I'm sure he was happy to pay the bill, y'all are both in happy relationships, there's nothing to regret.

[Skinhead-1979]

5 years ago is a rather long time ago and probably will raise some eyebrows. It could be taken completely the wrong way.

I wouldn't judge but certainly raise an eyebrow, and then decline.

[avery58]

Why not? Sounds like a good idea. It's been a long time and he probably forgot about it but I don't think he would be disappointed at getting some money he wasn't expecting. Maybe he'll use it to buy his girl a nice present or something for himself.

[Account]

It is weird and I can't help but feel that you are using that as an excuse to talk to him and I am almost certain that he would think the same.

[Retsam]

5 years ago? well let that go.
But for future after he goes to
pay, if I were you offer to pay your
part, most men won"t take your money
at that second BUT BUT BUT will
appreciate the fact you offered to
the heights degree. Shows your
good hearted and want to do your part.
2 beautiful qualities for most men

[poochigoochi]

i think 5 years is a long time, and he probably forgot about it already... if you are that guilty, maybe just quietly send him back the money and move on :D

[Alwayreckles93]

Girl your history. This guy probably doesn't remember you. That would be weird and very awkward. Just move on already. The guy is married I don't think his wife would appreciate your presence around him. Just live him alone.

[Static_In_The_Attic]

If you are going to pay him back after five years don’t forget to send him the money with interest as well.

[Apple1996]

Nah after all this time it'd be weird to pay him back or even care. He's probably far past remembering it

[loveslongnails]

I think that's a silly thing to do at this point. Forget about it and use the money for something you and your current boyfriend will enjoy together.

[spartan55]

Five years? Yes, I would think you were out of your mind.

[exitseven]

He invited you on a date and he paid for it which was appropriate.

[MicahRaine]

Naw don't stress about it. He's forgotten about it now.

[Staximus]

If you're not single then there's no reason to be opening closed doors. Forget about it.

[Jay-_-]

I'd think that you were thinking about me for five years 😂😭

[noohair]

You are 22 and 5 years ago you were 17? Don't live in the past. You can't grow in the past.

[WodensGedriht]

You should offer cause considering that makes you a good person.

[chrissykerdock]

that would be fruitless 5 years later

[slatyb]

Absolutely not. He doesn't care about it.

[DrPepper12]

Like Elsa said - let it go

[LiamJHayden]

Let it go. He has.

[Anonymous]

No, if you feel that bad donate it in his name

[Kelley1]

I don't believe you.

[HelpfulWoman]

5 years ago? nah

[Iron_Man]

Yes do it now