But at 52, the perennial bachelor is also at a point when prancing around with 30-year-old Rivera, a star of the subsequent generation, is going to cause more conversation than his love life has in the past. And what a love life it’s been.
“Went through a bit of a breakup recently,” he revealed. “And it was a little tough.” She asked who did the breaking up, and Spade deadpanned, “no comment.”
“No, obviously I’m the problem in every situation, but she was great—yeah, I sort of messed it up,” he said. Talking about the humbling experience of checking himself out in a mirror at Macy’s while buying a new shirt to get back “out there,” he self-deprecatingly referred to himself as a “6 or 7,” adding, “I’m OK with it at this point.”
Meanwhile, regardless of how real the connection was, pretty much every year of Spade’s life since the mid-90s is accounted for when it comes to being linked, attached, rumored to be dating or actually dating someone.
According to Spade, Boyle started seeing Nicholson and the two were involved in a car crash, after which a tabloid reported she crawled out of the sunroof, screaming, “‘I have a boyfriend! I can’t be here!'” He added, “That’s how I found out. She and I didn’t talk too much after that.”
Whether they dated or not, that’s certainly a nice thing to say about Spade.
“That stuff affects you in different ways, so I don’t really know where the damage is,” he told the New York Post while on his press tour for the book. “You can ask girls that date me that have a list of [my] problems they always want to show me. I’m sure that’s on there.”
“It’s going well,” the funnyman, who did take responsibility, said about fatherhood on Ellen in March 2009. “She’s starting to kind of know… not really who I am yet, but she’s getting it.” At the time, Grace was living in Missouri with Harper, but they would reunite for visits and the father-daughter relationship endures.
And perhaps, after a rough 2016, Naya Rivera was more than ready to meet a man who could make her smile.