McNearney and Kimmel definitely weren't love at "first sight." In fact, it took quite a while for the two to really notice each other. McNearney met Kimmel through her work as writer and later head writer on his show beginning in 2006, a position she kept and advanced with for 429 episodes through 2016 (Parade reports that she actually began as a writer's assistant in 2003). Beyond simply being coworkers, both McNearney and Kimmel were in different relationships. 

While it's difficult to find much info about McNearney's past relationships, Kimmel's are quite public. The comedian dated Sarah Silverman from 2002 to 2009, per In Style. The relationship with his future-wife blossomed soon thereafter, but all remain friends in this scenario. After some reasonable time to heal, the exes share nothing but smiles. Jokes Silverman in a 2018 appearance on Kimmel's show, "I mean, OK, Molly's cute. She's bright, she's funny, she's blonde, whatever, but come on! It's not fair! She gets new, woke Jimmy, I had 'Man Show' Jimmy."

McNearney clearly agrees, sharing of Silverman, "...I am extremely thankful to Sarah because I think she did a lot of good for Jimmy. I don't think that when a romantic relationship ends, a friendship should have to end," per Glamour.

Talk about a storybook romance, or should we say ... monologue?