Jennifer Aniston

The 50-year-old actress has had her fair share of relationships during and even before her acting career has bloomed into what it is today. Her first love was the actor, Daniel McDonald. The couple dated back for four years, from 1990 to 1994, before she made her screen debut on the popular and classic television series, Friends. Jennifer also dated Adam Duritz while trying to get over her tragic first love, but the relationship quickly died out. However, her first serious boyfriend was Tate Donovan, whom she dated from 1995 to 1998 and was even briefly engaged towards the end. Jennifer also dated a couple more A-listers throughout her career but no one comes close to her second love – Brad Pitt.

She and Brad met way back in 1998 and was one of Hollywood’s hottest couples. The power couple was married for five years, from 2000 to 2005, but much to everyone’s despair, the pair called it off in 2015. Jennifer was then married to Justin Theroux, but unfortunately, they hired lawyers and finalized their separation in 2017.