Joshua Burgin was one of the lamer guys that Rachel dated seriously on the sitcom Friends. He wasn’t really a jerk, but he was just so plainly boring. Though his actor Tate Donovan was Jennifer Aniston’s boyfriend IRL during the late 1990s.

And once again on the series, Rachel uses a professional environment to try to seek a new partner. For which, she has a lot of trouble because he was freshly divorced and disillusioned with long-term commitment.

I will say that her dressing up for him (and his parents walking in on that) was one of the series’ most memorable moments. I still can’t believe that she went out to dinner to wrongly prove that it was a dress and not lingerie. I definitely would not show up for a table for four in just my Magic Mike underwear.

He breaks up with her when she starts leading the relationship more forward than he wanted it to be. She unfortunately opened the door for him during a time that Rachel (and Monica and Phoebe) was going crazy with trying on wedding dresses.