Ashley Olsen with designer Marc Jacobs
Technically Ashley Olsen has been legal for a while. She turned 21 this summer, and if she had stayed in college instead of realizing that she was richer than sin and could have all the fun without the commitment of having to prove she learned stuff, she might be graduating now. I shudder to think of the crap I was up to at 21, but I’m married now with a toddler, and being in that situation makes you get nostalgic about near-constant hangovers punctuated by exams and random hookups. That was a long time ago for me, though, and I will probably never relive the chaos and stupidity of those years. Getting wasted and neglecting all responsibility does seem deceptively attractive compared to raising a three year old who screams his head off at the sight of bathwater. Maybe that’s what Whitney Bears is going through now.

Like Whitney, not everyone is willing to undertake the responsibilities that go along with the phase of life they’re supposed to be in. Hooking up with a hot young thing is often a way of reliving a youth that wasn’t that great the first time. Lance Armstrong is older than me at 36, but he still seems too old for Ashley Olsen. As a fit guy under 40, he’s not creepy-old for a 21 year-old, just in-denial old.

Both the NY Post and The Daily News are reporting that Lance and Ashley were all over each at a bar. This doesn’t make me go “ewww” so much as say “why?”

ODD couple alert: Ashley Olsen has a new, older man. The 21-year-old twin showed up to the Rose Bar at the Gramercy Park Hotel Monday night with Tory Burch’s ex, Lance Armstrong, 36. Our bar spy said, “They came together with a group of friends. Ashley drank red wine, sat on his lap and they were making out all night. They left together around 2 a.m.” Armstrong has been spending more time in town since he bought a home here. Another source said, “He tried to make Tory happy when they were dating by buying a place here, but she couldn’t deal with him not actually living in the same city, so they broke up.” Olsen’s rep didn’t return calls.

[From Page Six]

Lance was most recently dating some woman I’ve never heard of, fashion designer Tory Burch, who has an amazing six children and looks more Lance’s age and speed. He was also with singer Sheryl Crow for over two years following his divorce from the mother of his three children in September, 2003.

Ashley had a 30 year-old long-term boyfriend, Scott Sartiano, until recently, who was already too old for her.

Despite the questionable nature of this new relationship, I’m really glad to see this story today. I was looking for an excuse to publish these excellent pictures of Ashley Olsen’s Halloween costume. So go ahead and make out with guys who are nearly old enough to be your daddy, Ashley. As long as you can come up with inventive and non-slutty costumes like this, you get a pass.

Ashley Olsen is shown at a Halloween party with Marc Jacobs and his boyfriend. Pictures via ONTD.