The year was 1998: Jennifer Love Hewitt was the teen movie queen, starring in I Know What You Did Last Summer and Can't Hardly Wait, and Carson Daly was spending his afternoons being screamed at by overexcited teenagers on the set of TRL. The two got together, but the relationship crashed and burned a year later (but not before Carson got a tattoo of her name on his leg). Carson apparently found out that Jennifer had dumped him via Howard Stern's radio show — ouch. The two awkwardly settled their beef on air when Jennifer appeared on his talk show Last Call With Carson Daly in 2005, and he even congratulated her on her engagement to now-husband Brian Hallisay in 2013.