The designer, who started her own fashion label, the Row, with twin sister Mary-Kate, has been linked to other mature gentlemen, including 49-year-old film director Bennett Miller and 47-year-old Oliver Peoples CEO David Schulte, although she also allegedly dated the more age-appropriate Hayden Slater, the 33-year-old founder of Pressed Juicery.
For her part, Mary-Kate is married to 47-year-old French banker Olivier Sarkozy.
Ashley was spotted attending Philip Seymour Hoffman's funeral with Bennett back in late February as well, but clearly, their romance has gone the distance.
What do you think of Ashley's latest love interest?
He was previously married to author Charlotte Bernard, and has two children with his ex-wife -- son Julien, and daughter Margot.
But are we ready to see Mary-Kate and Ashley on the small screen again?!
"They were introduced and have started dating," a source told in February of the petite twin and Bennett.
“Mary-Kate was dancing with her husband, and Ashley’s boyfriend had his arm around her and was nuzzling her,” an onlooker tells Us Weekly.
“Richard had his arms all over Ashley, kissing and [stroking] her hair. He’s also close with Mary-Kate’s husband and was chatting with him.” While Ashley’s romance seems quite new, Mary-Kate and the French banker are approaching their one-year wedding anniversary.
Bennett and Benedetto may make for a particularly striking example (“Lovely fetus you’ve got there, ma’am, here’s my number, have it call it me in 18 years or so”), but older men getting romantically involved with younger women is hardly a rare phenomenon.
Every day, there seems to be another outrageous new celebrity coupling announced via pictures of some May-December frolicking: Jennifer Lawrence sharing a lollipop with Darren Aronofsky; Sean Penn dating Vincent D’Onofrio’s daughter; Mel Gibson having his ninth child with his 26-year-old girlfriend; Mary-Kate and Ashley Olsen double-dating with their 47-year-old and 58-year-old respective beaus; Leonardo Di Caprio’s sending another lady-love packing upon her reaching the ripe old age of 25.