Probably the longest running star cameo on the show, it’s hard to dislike Tom Selleck as Dr. Richard Burke.

He’s a childhood doctor of both Monica and Ross Geller and a personal friend of their father’s. So it gets really awkward when he actually decides to date Monica with that humongous age gap between them. Richard was a good guy, but that definitely was not a such a great move.

I’m actually surprised Jack Geller actually took the whole relationship better than I expected.

To be fair, he was one of Monica’s most loyal boyfriends. But she decides to break up with him when he’s adamant about not having another child because he had been there and done that and has grandchildren.

Eventually, he sees her again after the break up and they rekindle the romance a little but the whole situation reverts back to the same problem.

He enters the story once again when Chandler is about to marry Monica. And he makes it clear to Chandler that he still has feelings for her. But ultimately, he loses the fight for Monica’s heart.