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'I have the chance to date my old HS crush, but I’m engaged to my fiancee. What do I do?' UPDATED

'I have the chance to date my old HS crush, but I’m engaged to my fiancee. What do I do?' UPDATED


You play stupid games? You win stupid prizes, it's as simple as that.

"I (25M) have the chance to date my old HS crush (25F), but I’m engaged to my fiancee (24F). What do I do?"

I had a crush on this girl Carla since middle school going into HS but she never paid me no mind. I left for the military and met Sara, who is nurse and wants to become a doctor nurse practitioner! Sara was the usual type of girl I dated. I left the military to do contracting work, and moved back to my home state. One day while I was getting drinks at the bar, Carla was my bartender.

She didn't recognize me but when I told her my name she couldn't believe it. She said she couldn't believe how much I changed. I started becoming a regular, and eventually exchanged contact information with her to catch up. Throughout this time, she told me she has a crush on me even though she knows I have a fiancee. She said she likes how driven I am…now I'm conflicted.

She says that she'll give me time to think about what I wanna do. My fiancee and I are doing great, but I feel like she's normally the type of woman I always get. Carla, I never had the opportunity or thought I would. I don't wanna hurt Sara, but feel like I would regret this forever if I don't pursue it.

The internet did not hold back on OP.

Fearless-Adeptness61 wrote:

“Starting to become a regular” at bar. No you’re going to visit your crush.

Exchanged numbers while in relationship.

Cheating is a series of choices and it starts here.

You know, most people wait for these type of opportunities when their high school crush or b*lly meets them later in life and they get their glow up revenge, double middle fingers in the air, because now they look better and doing better in life than their high school counterpart and instead of doing that.

You’re thinking about trying to get laid by someone who didn’t give you the time of day in HS while you have a fiancé. The joke is you’ll end up with neither of them.

gojocopium wrote:

Dump Sara so she can find someone who actually values her.

You can go after a woman who's fine with pursuing taken men. Y'all deserve each other.

RecordingKindly3074 wrote:

So she paid no mind to you for years sees you again and decided yeah he’s taken I want that man you must be dense she was crush from middle school it’s been what 7 years since you seen her and you found someone who seems to love you but you want to dump her for someone your lusting yeah you don’t need to get married.

_dogs_ wrote:

You absolutely should not be marrying someone if you're considering something like this. Try to feel empathy for just a minute here. Imagine what it would feel like if, five years down the road, your wife told you she almost left you before the wedding because her high school crush said they wanted to date her. How small and unappreciated would you feel?

How f#$ked up would you feel if she then told you she stuck with you because you're "the type of person [she] usually gets."

Do yourself and your fiance a favor and end this doomed relationship dog. She deserves better and you really need to work on yourself.

Winstonisapuppy wrote:

You’re not ready for marriage. I see two things happening here. Either you’re going to break off your engagement with a woman who has been good enough to see yourself spending your life with up until now to be with your crush.

Your crush will never live up to the fantasy you’ve had for over a decade and you’ll regret your choice. Or you’ll stay with your fiancé but always wonder what could have been with your crush and end up regretting your choice and resenting your wife.

You’re obviously not committed to a future with your fiancé if this encounter was enough to derail your commitment. My advice is to leave your fiancé and let her find someone who actually loves her and wants to have a life with her. And you’ll be free to have a disappointing fling with your middle school crush or be single and find someone you actually love.

A few weeks later, OP jumped on with a messy update.

I broke her heart. I love Sara so much, and I stupidly called off the wedding to be with my old crush a few weeks ago. Throughout the couple weeks, Carla used me as a piggy bank. That’s all I f#$king was to her. I spoiled her, paid for her hair, nails, etc. I gave her everything.

I found out she used the money I Zelled her to buy a ticket for some guy to come see her. I’m sick to my stomach. I reached out to Sara, but she feels betrayed and said she doesn’t want to be a sloppy seconds, but she’s not. I love her and needed this to realize it.

Commenters did NOT feel bad for OP one bit.

sav575757 wrote:

Have you ever heard the phrase, "Play stupid games, win stupid prizes?"

If your ex-fiance has any self-respect, she won't take you back. You've already discarded her. Leave her alone.

thefflt wrote:

I remember your last post and honestly, I love this for Sara. She's free, Carla's a ho, and you're miserably single.

Everybody got their best ending.

Lost-and-dumbfound wrote:

You committed to Sara, saw your high school crush for a second then abandoned Sara for this other woman and it’s only because she screwed you over that you want Sara back. Do you think she has zero self respect?

I mean you clearly have none for her so let’s hope she was more than the respect you have for her and tells you to leave her the f#$k alone. You can’t dump your fiancee for another woman and expect any type of forgiveness or redemption. You made your choice. You lost Sara. Live with it.

Fit-Secret8346 wrote:

So a month ago you were here saying you had the chance to be with your HS crush and all of the internet called you foolish and that you weren't seeing Carla for what it was. You were so sure she only wanted a "relationship." Everyone told you not to mess up.

Well, you went and messed up anyway and had the exact consequences the internet told you you would have. A comment on the previous post did mention that "you'll end up with neither" and that's exactly what happened. You made your bed, now lie in it. Leave your fiance alone and don't insult her intelligence anymore. And don't think anyone's buying your delusion of "bUt I LoVe HeR."

MyUserNameisMehhh wrote:



You don't love Sara. Leave her the f#$k alone.

I knew this felt familiar. You posted a month ago. It took you A MONTH to realize Carla didn't give a s**t about you.

KrazyKirbyKun wrote:

Question because you're already getting torn apart in these comments for the obvious. There's a lot I can say about playing stupid games and whatnot, but I want to come at you with a sense of neutrality. But what is it about Sarah that you love exactly? Outside of the things that she does for you or makes your life easier.

Well, this was certainly a heaping dose of schadenfreude.

Sources: Reddit
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