Grab Your Alibi And Join True Crime Tribe

Her Boyfriend Goes On Dates With His Ex Every Friday Night, And It Makes Her Uncomfortable

profile Bre Avery Zacharski | Apr 25, 2026
Apr 25, 2026
An elegant lady in a short black
Aleksandr - stock.adobe.com - illustrative purposes only, not the actual person

Most couples have a few quirks they agree to overlook, like questionable taste in reality TV or the way they load the dishwasher all wrong. But weekly dinner dates with an ex just might be where the line gets drawn.

This 29-year-old woman has been dating her 32-year-old boyfriend for the last four months, and he’s a pretty perfect guy. He’s sweet, thoughtful, and supportive of her.

He has been diagnosed with ADHD and autism, and she’s never dated someone like that before, so she’s trying her best to figure out how to communicate in a manner that caters to him.

She actually was talking to her boyfriend for six months before they moved in a romantic direction, and he always used to tell her about his female friend C.

C has been in her boyfriend’s life since they were little, and she’s his best friend’s sister. She was clued in to them dating in the past, and her boyfriend stated that the relationship fizzled out after C came out of the closet.

“Last week, something new came up. He mentioned that about a year ago, he and C were actually dating again, but split up because she came out as gay,” she said.

“When I asked more about it, he explained that they’ve been on-and-off for over 10 years, dating other people in between but always coming back to each other.”

“I also found out that they don’t just hang out in a group like I’d assumed. They see each other every Friday night, just the two of them, watch horror films, and get takeaway. This is something they used to do when they were together and have continued doing.”

Well, she felt extremely uneasy after finding this all out, because it does look like her boyfriend is having dates with his ex every Friday night.

An elegant lady in a short black dress walks along the terrace. Summer sunny day. Fashionable woman portrait.
Aleksandr – stock.adobe.com – illustrative purposes only, not the actual person

Sign up for Chip Chick’s newsletter and get stories like this delivered to your inbox.

She very politely pointed this out to her boyfriend, who promised to change that in order to make her feel better. Except last night, he went out on his date with C.

She addressed this yet again with her boyfriend, who defended himself by saying he has to be free to hang out with his friends. She’s not trying to be controlling and doesn’t want her boyfriend to sacrifice friendships for her, but this feels like he and C are more than buddies.

“But this specific situation feels different to me, given their history, and the fact it’s a regular one-on-one thing that mirrors what they did as a couple,” she continued.

“How do I approach this in a way he’ll understand without it turning into an argument?”

Um, this is super bizarre, and we can’t blame this on her boyfriend not picking up on social cues because of his autism or ADHD. He is genuinely acting like he’s still serious with C, and on no planet is that acceptable.

He knows exactly what he’s doing and how wrong it is. Also, I am not buying that C likes girls now after spending an entire decade with a man; that just reads like a convenient story he concocted to make her less suspicious of them.

Since C and her boyfriend always manage to find a way back to one another, I think she’s a placeholder until that happens.

What do you think?

You can read the original post below.

screenshot
Pictured above is a screenshot of the original post for you to read

image5
By Bre Avery Zacharski

Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski