My friend Jessica* met a guy named Mike on JDate and they’ve gone on a bunch of dates already. On their fifth date he came to her place to pick her up and asked her if it would be okay to stop by a friend’s house for an hour where a bunch of his friends would be. She said sure, after all it meant he wanted her to meet his friends, and they headed off. It wasn’t until he rang the doorbell that he told her that the hostess was his ex-girlfriend. They’ve been “just” friends for a couple of years and she has a serious boyfriend now. Jessica was stunned. It wasn’t a huge deal, but it would have been better for Mike to have been straight up about whose party it was from the start. 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 her. But in an effort to befriend Jessica, the ex made some of the most inappropriate comments and asked some of the most inappropriate questions I’d ever heard. She tried to bond with Jessica by asking her if she was also annoyed by waking up in Mike’s bed to find his cat sitting on her head. Well, this being Jessica and Mike’s fifth date, she hadn’t had the privilege of spending the night yet but didn’t feel that was information she needed to share. Then the ex told Jessica she wished that Mike would teach her new boyfriend how to give a body massage. Again, not an experience Jessica had yet had and found the entire situation incredibly awkward. I think the ex may still have feelings for Mike and I have no idea if Mike is oblivious to this or just playing dumb.

How soon is too soon to introduce a new date to an ex that you happen to now 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 the number of dates you’ve been on on both hands, 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 totally inappropriate, then it’s too soon. If you have any inclination that you’re ex might still have feelings for you, then it’s too soon. This goes for both girls and guys. Meeting an ex is intimidating and even more so when the ex mentions intimate tidbits.

Jessica was a class act and didn’t exchange any information besides to say 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. It bugged her and she is filing away the information in the back of her mind but the experience didn’t eliminate him. After all, it was his ex that was acting classless, not Mike. I told her that, in the future, if Mike were to ask if she wanted to hang out with his friends that she should nonchalantly ask which ones before agreeing. If the “friends” once again included 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!

*all names have been changed