How Long Have Peter Weber and Kelley Flanagan Been Dating?

After getting engaged to Hannah Ann Sluss and trying things out (for two days) with Madison Prewett, Peter Weber is officially dating Kelley Flanagan.

On May 2, Weber posted a photo of him and Flanagan kissing in an airplane he was piloting. “You caught me. Let the adventure begin,” he captioned the post.

Kelley Flanagan and Peter Weber on 'The Bachelor'
Kelley Flanagan and Peter Weber | Francisco Roman via Getty Images

For weeks, rumors have been swirling around that Weber and Flanagan were officially together but they were hesitant to go public. But when did Flanagan and Weber start reconnecting after The Bachelor stopped filming?

When Weber went on The Viall Files, he provided a timeline… of sorts. Here’s what we make from all the info he gave.

How Peter Weber and Kelley Flanagan reconnected, according to the former bachelor

The pilot told Viall that he and Flanagan ran into each other at the Super Bowl back in February. He says they said hello but he didn’t ask for her phone number or anything. Then, they ran into each other again a bit later when they were out in Los Angeles with friends. According to Weber, that’s when they exchanged numbers and began talking.

View this post on Instagram

You caught me. Let the adventure begin

A post shared by Peter Weber (@pilot_pete) on

Once Weber and Flanagan had been chatting for a bit, Flanagan told the pilot about some “family” stuff she had going on, so Weber flew to Chicago to “take her mind off” things. When he was in Chicago, Americans were advised to begin social distancing. So he decided to hunker down with Flanagan and another Chicago friend, Dustin Kendrick.

Nick Viall’s post with Kelley Flanagan

But what really provides an extra look at the Weber, Flanagan dating timeline is a comment Viall made about an Instagram photo he posted with Flanagan.

On March 12, Viall posted a photo of him and the attorney at an event. He captioned the post: “She’s not with Peter.”

View this post on Instagram

She’s not with Peter

A post shared by Nick Viall (@nickviall) on

“I met Kelley–it’s funny because I posted this picture–and I didn’t think you guys were hanging out or anything was going on. And I’ve told this story on my podcast, but I texted Kelley and I was like, ‘Hey, I have this perfect caption: Not with Peter,’ which is not saying anything other than the fact that she’s literally not with Peter. And I remember her being like, ‘Ehhhh.’ And I was like, ‘This is a harmless f*cking caption. What is the problem?’ It makes a lot of sense now,” said Viall after learning that Weber and Flanagan had been talking by that point.

Based on Weber’s interview with Viall, it seems the pilot and Flanagan began talking somewhere between the Super Bowl (February 2) and when Viall posted that photo (March 12).

But some fans have a theory that Weber and Flanagan got together after the former bachelor’s split from Sluss. Flanagan was at the finale, after all.

Read more: Wells Adams Wants Peter Weber and Kelley Flanagan on ‘Bachelor in Paradise’ If They Break Up