Even the most romantic gestures can fall flat if the timing’s off.

After winning a bet and spending big on a special night out, his girlfriend met him with disappointment instead of gratitude when he failed to listen to her preferences.

Read on to find out how it all went down.

AITA for breaking up with my girlfriend after she refused to go on a nice date I planned because it was on a Wednesday?

I (27M) recently hit a small parlay win and decided to do something special for my girlfriend (25F).

We have been together for almost a year and things have been good, but she always says she wants me to plan more thoughtful dates.

So this time, he thought he had planned the perfect night.

So I booked us a reservation at this really nice restaurant she always talks about—hard to get into, amazing chef.

I spent $800 total on the reservation, drinks included.

It was for a Wednesday night because that was the only time I could get a table.

But when he finally revealed his grand plan, his girlfriend didn’t react the way he expected.

I told her it would be a surprise, and when I finally revealed the plan, she looked disappointed.

It all came down to a scheduling conflict.

She said Wednesday was a bad day for her—she has work early the next morning and would rather do something on a Friday or Saturday.

The two argued back and forth.

She said she would rather do “a multi-event thing,” like dinner then a show or bar hopping, and asked if I could cancel and reschedule.

I explained that this was a special reservation and the timing could not be moved.

Also, that I could not afford to do something like this without the parlay win.

She said she appreciated the gesture but still would rather do something else on a weekend.

No compromise. No “let’s make it work.”

Just flat out no.

The ordeal made him second guess the entire relationship.

That made me feel like nothing I did would ever be enough—like it was more about the vibe than the effort.

So I told her if this is how she reacts when I try to do something special, then maybe we’re not right for each other.

And I ended it.

But then he started doubting himself again.

Now my friends are saying I overreacted, and I’m lowkey thinking I might have.

AITA for walking away over this?

Sure, it’s a letdown, but is this guy really deserving of any sympathy here?

Reddit didn’t seem to think so.

This user thinks he should reserve his generosity for someone who actually deserves it.

This commenter is less than sympathetic.

Perhaps a little more foresight was in order for a reservation this expensive.

He really should have checked with her first.

He wanted to surprise her with something grand, but forgot that thoughtfulness starts with listening to your girlfriend’s preferences.

He may be skilled at betting, but this time, he took a gamble and lost.

If you liked that post, check out this story about a guy who was forced to sleep on the couch at his wife’s family’s house, so he went to a hotel instead.