Somehow, Peter Weber's journey for love is extending well beyond his season of The Bachelor. After proposing to Hannah Ann Sluss , he ended things a month or so later to give things a shot with runner-up Madison Prewett . Two days later, they had split as well. Now, Peter has been spotted out in Chicago with none other than Kelley Flanagan , a contestant from his season who made it Peter's top six before being sent home. However, they've always shared a bit of a connection thanks to the fact that they bumped into each other for the first time before filming. An onlooker who caught their Chicago reunion on video tells us what she thinks is going down between the pair. Third time's the charm?