The Daily Grind Video
ABC's "Bless This Mess" - Season Two

Source: Ali Goldstein / Getty

Everyone has an opinion on Insecure characters, but it’s safe to say that both Issa (Issa Rae) and Molly (Yvonne Orji) have made some questionable dating decisions.

It seems like Molly is just now getting her act together with her “Asian Bae” Andrew (played by Alexander Hodge). But let’s not forget how she was the queen of picky back in the day. In one instance, she wanted a man to give her reassurance by the hour (Dr. Michael Pete played by Brandon P. Bell). In another instance, she couldn’t deal with a man’s sexual past even though it had nothing to do with his relationship with Molly in the present (Jared played by Langston Kerman). Then, there were other times when her unwillingness to commit was understandable (everyone can’t get involved with a married man no matter how open his marriage is – Dro played by Sarunas Jackson).

Issa has also had some challenges. There was that one time she cheated on her long-term boyfriend with a music producer – Daniel played by Y’lan Noel. Now, with the recent episodes of season four, it seems like she’s trying to reconnect with Nathan (played by Kendrick Sampson) when they still haven’t had the discussion about why he ghosted her in season three.

The possibility of Issa getting back together with Lawrence (played by Jay Ellis) also hangs in the air and he too has had his ups and downs with exes.

Despite the challenges of each character, they’ve still had a solid selection of past romances. Although the exes weren’t perfect, they definitely had some redeeming qualities and weren’t bad to look at either. Check out some of the exes played by Y’lan Noel, Jidenna, Brandon P. Bell, DomiNque Perry, Langston Kerman, Christina Elmore, Leon Thomas III, and Sterling K. Brown below.

It’s definitely a stroll down memory lane.