My friend Jessica has been on a bunch of dates with this guy named Mike, whom she met on JDate. On their fifth date, he came to her place to pick her up and asked if it would be okay to stop by a friend’s house for an hour before dinner because a bunch of his friends were getting together.She said sure, and they headed off.It wasn’t until he rang the doorbell that he told her the hostess was his ex-girlfriend.Um... thanks for the heads up! Mike explained that they’d been “just friends” for a couple of years and that she now had a serious boyfriend. Still, Jessica was stunned. It wasn’t a huge deal, but it would have been better for Mike to have been straight up from the start about whose party it was.There was no going back at this point, so Jessica pasted a smile on her face and introduced herself to the hostess.Mike’s ex-girlfriend was incredibly friendly and tried to get chummy with Jessica. But in an effort to befriend her, the ex made some of the most inappropriate comments and asked some of the most inappropriate questions I’ve ever heard.She tried to bond with Jessica by asking if she also was annoyed by waking up in Mike’s bed to find his cat sitting on her head. Well, this being only Jessica’s and Mike’s fifth date, she hadn’t yet had the privilege of spending the night, but didn’t feel it was information she needed to share. Then the ex told Jessica that she wished Mike would teach her new boyfriend how to give a body massage. Again, not an experience Jessica had yet had, and she found the entire situation incredibly awkward.Finally, the ex boasted to Jessica that it was because of her that Mike used chapstick and had soft lips.Thanks for the info, lady.I think the ex may still have feelings for Mike, and I have no idea if Mike is oblivious to this, or is just playing dumb. I’m thinking it’s the latter, and he’s just choosing to ignore it and avoid confrontation. They have so many mutual friends now that to admit he knows that she has feelings for him will make things awkward in their group.So how soon is too soon to introduce a new date to an ex that you now happen to be friends with? If you have to lie about where you’re going until you’re at the door, then it’s too soon. If you’re still able to count on one hand the number of dates you’ve been on, then it’s too soon.If you haven’t yet had “The Talk,” then it’s too soon.If your ex doesn’t know how to be nice without being inappropriate, then it’s too soon.If you have any inkling that your ex might still have feelings for you, then it’s too soon. This goes for both girls and guys. Meeting an ex is intimidating, even more so when the ex lets out intimate tidbits.Jessica was a class act and didn’t exchange any information besides saying that she and Mike had just recently started dating. She also didn’t mention any of this to Mike because she didn’t want to start any trouble.But it did bug her, and she is filing away the information in the back of her mind in case there are other red flags in future – however, the experience didn’t eliminate him from being a dating prospect.After all, it was his ex who was lacking class, not Mike.I told her that in future, if Mike asks if she wants to hang out with his friends, she should ask, nonchalantly, which ones before agreeing. If the “friends” once again include his ex, she should say that she’d rather just hang out with him one-on-one some more.No guy is going to have a problem with that! Neither I nor “S” are friends with our exes, and don’t see any reason to be. Prior to meeting “S” I had thought it was okay, but now that I’m with my bashert, I don’t have any desire to socialize with people I was once romantic with; and I respect “S” too much to put him in a position where he might feel awkward.I know people who truly are friends with their exes – their relationship ended eons ago and there is absolutely nothing between them – and if their current significant others are comfortable with the friendship, then that’s great.I wouldn’t be, and luckily I don’t have to be. Each couple have to cross that bridge when they come to it, and decide what will work for them.