Allegra Riggio Reveals Exclusive Details About Being Miserable with Fiancé, “Mad Men” Star Jared Harris

Sugar Daddy Jared Harris Allegra RiggioIf you’re dat­ing an older man, you’ve prob­a­bly been asked at least once about what the two of you could pos­si­bly have in com­mon when there’s such a big age dif­fer­ence. When 52-year-old Mad Men star Jared Har­ris met his 38-year-old fiancée, Alle­gra Rig­gio, back in 2009, they instantly shared some­thing: mis­ery. At the time, Har­ris was just com­ing out of his messy divorce, while she was in an unhappy rela­tion­ship of her own. Iron­i­cally, the celebrity cou­ple met at a com­edy club, where a mutual friend was performing.

On the heels of her upcom­ing wed­ding to Har­ris, Rig­gio revealed what it was really like that first night she met her older soon-to-be hus­band, and how that chance encounter turned into a real May-December relationship—and now a marriage.

Rig­gio met Har­ris again the day after at the same club and invited him to join their table. The pair got to talk­ing, only to find out that they had way more in com­mon than they thought—they were both utterly mis­er­able. Nat­u­rally, they exchanged con­tact infor­ma­tion and resumed their own lives, although Har­ris was always at the back of Riggio’s mind. “I’d text Jared every month to make sure he hadn’t drifted fur­ther into the abyss, and we’d change some pleas­antries here and there, but we never made plans. Which was fine, as I hadn’t planned on dat­ing him.”

After Riggio’s painful rela­tion­ship ended, she called her “mis­ery friend” for a fun night out. That night marked the start of this celebrity couple’s May-December rela­tion­ship. Soon enough, their shared mis­ery turned into hap­pi­ness. The celebrity cou­ple agreed to stay away from mar­riage, hav­ing been tainted by their past relationships.

Four years later, Har­ris pro­posed. “My life since meet­ing Jared has been noth­ing short of won­der­ful, and love-filled. Life is good, and gets better.”

This celebrity couple’s story is proof that age is irrel­e­vant when you find some­one that you really con­nect with. Had Har­ris and Rig­gio let their 14-year age dif­fer­ence stop them from get­ting to know one another, they wouldn’t be where they are today. So, whether you’re casu­ally dat­ing an older man or look­ing for some­thing more seri­ous, let this be a les­son learned—anything is pos­si­ble when it comes to May-December relationships!

What do you think: Would a big age dif­fer­ence stop you from get­ting to know a man who you were attracted to?


Takeda, A., “Exclu­sive: Mad Men Star Jared Har­ris’ Fiancee Alle­gra Rig­gio Shares the Story of How They Fell in Love,” Us Weekly web site, Octo­ber 29, 2013;

Photo Credit: Joe Seer /