Skip to Content

Running it back?

On August 10, Peter Weber and Kelley Flanagan were spotted at a Chicago Cubs baseball game by a number of observers, one of whom runs the Instagram account @bachelorteaspill and went public with the unexpected sighting.

Why do we classify this sighting as unexpected?

Because Weber and Flanagan dated for about a year after the former wrapped up filming on his season of The Bachelor… and things did NOT end well.

The reality stars split way back in February 2021.

“We had a great Valentine’s Day together. And then, again, there were just like little things. … It ended really badly,” Flanagan admitted on the Chicks in the Office podcast in May 2021.

“I essentially went off on him. I ended up leaving New York and going to one of my girlfriend’s houses and hanging out with her.

“He texted me, I didn’t respond and then found some news out that I wasn’t happy about.

“We still had each other on Find My Friends. … I went off and essentially said, like, ’Get the hell out of my life.’ It ended really badly.”

Kelley Flanagan and Peter Weber Together

Flanagan didn’t delve into specifics, but she also said just enough to make it fairly easy to assume Weber wasn’t honest in their relationship.

Or loyal.

“There’s a lot of things that you hear, this world is very small, I get stopped by girls in Nashville and they’re like, ‘My friend hooked up with Peter last week,’” Kelley added after the break-up.

It sounds very much like Weber was cheating on her.

This is the same person, remember, who chose Madison Prewett to be his Bachelor winner… only to dump her weeks later… only to then date contestant Hannah Ann Sluss for a bit… only to also dump her start dating Flanagan.

Peter Weber and Kelley Flanagan Throwback
Photo via Instagram

Also in May of last year meanwhile, Peter got personal on his and Dustin Kendrick’s Bachelor in the City podcast.

“I’m 100 percent moved on,” the often-horny pilot said at the time.

“I’m so thankful for our time together. But I know that Kelley and I aren’t meant to be together and that’s okay.”

That all sounded nice and amicable, but Weber also labeled his ex as “calculated [and] very disingenuous” for what she said about him after the two went their separate ways.

Peter and Kelley (The Bachelor)

But might the former lovers now be back together?!?

Neither has commented on the August 10 Chicago sighting just yet.

“Peter and I had a lot of fun, but I don’t know if I looked up to him in the way that I wanted to look up to my spouse,” she added just over a year ago.

“I have this with my brothers and my dad, where if I’m in a moment where I need some sound advice and look for who to go to on important decisions, but with Peter, it was just fun and games.

“I could have fun with him but I wanted more of a man that I look up to. I just didn’t look up to Peter in the way that I always hoped I would look up to my husband.”