October 17, 2026 at 8:20 pm

She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

by Michael Levanduski

Waitress flirting with customer

Shutterstock

When you are in a relationship with someone, you should not be keeping secrets or doing things that could hurt them.

What would you do if you found out that your boyfriend had been giving massive tips to one specific waitress at a bar he goes to with friends each week? And, to make it worse, you then found out that he had also sent her even more money via CashApp?

That is what happened to the woman in this story, and she feels like it is a betrayal even though he says it is innocent and only because she is a good waitress.

Personally, I would consider this a form of cheating. Read through the full story below and see if you agree.

AIO – partner has been sending money to another girl

My partner 32M and I 25F have been together for 5 years and have never had any serious unfaithful issues occur.

You can’t be too careful with situations like this.

However, the past month my partner has been getting close to a server at a local bar that he goes to weekly with coworkers.

We went out a couple weeks ago and he was intoxicated, spotted her and was hugging up all over her 28F .

Yeah, this is not appropriate.

There was a certain sparkle in his eyes that a girl can see- a type of look of infatuation. Apparently she’s a “really good server” and when he goes out with his coworkers, he will tip her over 60%-100%+ of the tab, typically being about $50-100 everytime he sees her (for like a $30 order).

I love that he every once in awhile he goes above and beyond- but this is every single time requesting this one girl every week.

This is absolutely a betrayal of trust.

Here’s where I felt hurt and I admit I invaded privacy. My gut instincts were have been TELLING me something is off, so I checked his phone when he wasn’t around and saw on cashapp that he has been sending her ADDITIONAL money.

About $200 the past month. Which really annoys me because he refused to download cashapp to send me money when needed, but now uses it multiple times to send her money.

I would consider this a form of cheating.

The fact that he decided to privately send her additional money is what hurts me and I feel this is a form of flirting/something more .

Of course, for him “it’s his money; he can do what he wants with it” and “she’s a really good server.”

Her feelings of betrayal are completely understandable.

We haven’t talked in the past day but I still haven’t confronted him specifically about it. I just told him I don’t want to talk right now.

I truly felt hurt with my findings and just feel odd, I don’t feel jealous necessarily.

Am I overreacting?

She is not overreacting in the least. If anything, I would say she is underreacting. Not only because he sent her the money at all, but also because he didn’t tell her about it.

Read on to see what the people in the comments thought about this story.

Whether the behavior has gone beyond sending money or not, it is inappropriate.

Comment 5 79 She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

Here is a comment from a female server.

Comment 4 84 She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

This commenter says to leave him immediately. I agree.

Comment 3 87 She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

He is showing her who the priority is.

Comment 2 90 She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

If you enjoyed this story, check out this post about a sister who feels badly about unknowingly encouraging her younger brother to play with bullies.

This person thinks the waitress is just flirting for the money.

Comment 1 89 She Discovered Her Boyfriend Was Tipping a Cute Waitress Huge Amounts and Sending Her Money on CashApp. He Says It’s Innocent

There are many forms of cheating out there, and this is most certainly one of them. He is keeping secrets, sending money to another woman, and who knows what else.

This lady needs to end it now before it gets worse.

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Senior Contributing Editor, Workplace & Community

Michael Levanduski is a veteran journalist and digital culture specialist with over 15 years of professional writing and research experience. While his background spans emerging technology and complex technical subjects, Michael specializes in analyzing workplace ethics, property disputes, and viral interpersonal dynamics across modern digital forums.

Since joining TwistedSifter in 2024, Michael has authored some of the publication’s most widely read coverage on corporate policy, malicious compliance, and neighborhood relations. Rather than simply aggregating online debates, he brings rigorous research, organizational context, and an empathetic editorial voice to everyday human dilemmas—transforming raw forum discussions into insightful, highly engaging narratives.

When he isn’t covering internet culture, Michael enjoys traveling, keeping up with tech trends, and spending time with his family. Connect with Michael on LinkedIn and Facebook.