A Brief History of Paul Rudd Hooking Up With Every Cool Girl Ever in His Movies

The lady: Jennifer Aniston

The movie: Wanderlust + The Object of My AffectionThe deal: In Wanderlust, they're a city-rushed couple who rediscover themselves--and each other, and, um, others--at a hippie retreat. Though their relationship is in tatters, they have that believable but-we're-each-other's person thing going down pat, probably thanks to The Object of My Affection--a rom-com classic if there ever was one. Nineties Jen pines for gay Paul--but their love proves to be deeper than romance.

The lady: Reese Witherspoon

The movie: How Do You Know? + Overnight Delivery

The deal: I know, not a lot of us saw the first one. Suffice to say, it takes Paul the whole darn movie to convince Reese to be with him. Reese, whatsa matta with you? Oh, you were dating Owen Wilson? All right. We'll let it slip this one time. Only because in Overnight Delivery, you showed a wounded Paul the light, after that jezebel Christine Taylor broke his heart.