5. Jon Hamm and Jennifer Westfeldt
From 1997-2015, Mad Men actor (and dad bod flaunter) Jon Hamm was in a serious relationship with Kissing Jessica Steinwriter and actress Jennifer Westfeldt, who is arguably much hotter than he is. Jon and Jen both have tons of movie and television credits to their names, and as recently as August of this year there have been rumors of the longtime lovers being back together. The story goes that after so long together (an impressive 18 years, which is an eternity in Hollywood), the two struggled to cut each other off completely.
Originally, they called things off because he wanted to have children and she did not. They had agreed they did not need to get married, but the children thing was too big to ignore, I guess, and it led to their going separate ways. Whether or not their reconciliation is for real or just another tabloid rumor is uncertain, but both parties have said they are still there for one another, and both have films being released in the near future.
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