Can I date my friend’s ex?

Hi all. I hope yesterday went OK without me. I had a very nice day off and bought two bottles of the last wine on this page at the Westport Rivers Winery. Nothing like dessert wine. But enough about my big day off. Let’s get going.
Q: Hey Meredith, I’m 35 & single. Friends want to set me up w/ 2 different men who dated my girlfriends in the past. I’ve asked around & got very different responses. Case #1: my college roommate dated “Jason” 16 years ago. I’m still good friends w/ the girl, (she lives in Atlanta, is married w/ 2 kids). In full disclosure, Jason WAS the love of her life -- he broke up w/ her & at the time broke her heart, college ended & they lived far apart. Another friend remained close w/ Jason & now wants to set us up. Case #2: my friend dated “Bill” 2 years ago for a few months. She blew Bill off for another guy, it didn’t work out & she tried to get Bill back. Bill is single again, she called & he is apparently uninterested. She met bill through MY friend – who now wants to set me up with him. Full disclosure, she says breaking up with Bill was the biggest mistake of her dating life. Also, I have very few single GFs left. What’s your opinion on being set up with men my friends dated? Can girls stake their claim on guys forever? Do I have to ask permission? Both are good, quality guys – they’re gonna date someone, why not me? Also, if either guy was mean in any way to my friends – I’d never consider dating them. Also, I didn't seek them out. -- On-the-Fence, Boston

OTF, if these relationships had not happened two and 16 years ago, I’d tell you to run from both men to preserve your friendships. But … you’re 35, these guys sound like they have potential, and in one of two cases, your friend has already married someone else. Here's what I'd do: I’d ask both setter-uppers to orchestrate informal social outings with these men -- group activities, not dates. Feel it out. See if you could actually be interested in these guys. If either of them floats your proverbial boat, I’d approach your friend(s) and tell them what's going on and how you feel. No one wants to see a friend with an ex, but a good friend will want to see you happy. For the record, I’m more worried about Jason’s ex than Bill’s ex. Even though that relationship happened 16 years ago, the break-up wasn’t up to her and she convinced herself he was the love of her life. In the case of Bill, it was a short-term thing. Your friend blew it, and now she's being overly dramatic about the loss. She barely knew him. I think it's safe to meet these guys and interact with them. Then, if it's worth it, approach your friends. And brace yourself – you might not get a good initial reaction to “Can I date your ex?” – but if your friends really see the potential for you to be happy, they’ll come around. Readers? Agree? I’m hesitant about this advice – friends don’t let friends date exes – but in this case, based on age, place in life, and other factors, I think it’s worth some careful exploration. Tell me your thoughts here. Submit a letter to the right. Twitter here. -- Meredith