The fifth time may be a charm for notorious philanderer Jesse James.

The motorcycle customizer, whose failed high-profile relationships with actress Sandra Bullock and tattoo artist Kat Von D made headlines, will reportedly walk down the aisle for a fifth time.

James is allegedly engaged to Alexis DeJoria, a drag racer and heiress to the Paul Mitchell fortune, according to Hollyscoop. DeJoria is the daughter of John Paul DeJoria, co-founder of the hair care giant.

RadarOnline was the first to report on James dating DeJoria in October.

"Jesse and Alexis have been dating for a little over a month,” a source told RadarOnline.com. “They bonded over their love of motor-racing, Alexis is a rookie in the professional ranks of the National Hot Rod Association and competes in the Tequila Patron Nitro Funny Car and one of Jesse’s companies used to sponsor a mutual friend’s race team, so naturally their worlds collided."

“Jesse has been helping her compete, he’s been hanging out in her pit area during races, passing on his expertise to the team of mechanics and was even spotted helping Alexis pack-up her parachute after a race," the source added. "And their love of motorsport isn’t their only common interest – like Jesse, Alexis is fond of the body art world and has many tattoos."

When a fan criticized DeJoria, 35, for getting engaged to James after only a month of dating, the drag racer didn't attempt to deny anything, according to USA Today. "Am I supposed to wait till I'm married to sleep with a man too?! Lol! You've been brainwashed into what society says is right," DeJoria replied.

The fan's concern may be justified, as the former CEO of the now-defunct West Coast Choppers has a history of cheating.

Bullock filed for divorce from James in 2010 after five years of marriage after she learned he had cheated on her with multiple woman. Von D broke off her engagement with the 43-year-old after learning he had cheated on her with at least 19 women.

James was also previously married to Karla James and adult film star Janine Lindemulder, according to "Access Hollywood."

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