I have a very bad habit that I’m fully able to acknowledge is a very bad habit; however, I still can’t seem to break this very bad habit. I’m fully aware that I need to stop comparing the women I go out with to a specific ex-girlfriend that I dated for a long period of time, and went through a difficult break up with almost two-years ago yet, up until my date yesterday, I still did it.

It could have been because I had a long day at work, or maybe it was the fact that I was running late and thus rushing to make it on time, or maybe it was just a change in the weather, I don’t know, but in any case my date yesterday was the first time I went out with a woman and didn’t compare any aspects of the date, or her, to my ex-girlfriend.

Of course I don’t expect that if I see this woman again that I will never think of my interactions, or perhaps eventual relationship, with her in comparison to my past one; but the fact that I didn’t do it on our first date was encouraging. At 27, I am well aware that I am carrying some substantial baggage but, then again, so are the women who I go out with and for both of us that’s okay.

Perhaps it’s strange that I compare the women I go on dates with to an ex-girlfriend, and certainly I’m not going to announce this to any of them, but perhaps the fact that I didn’t do it yesterday signals that, while I’ll never forget my ex-girlfriend or our relationship, I’m ready to stop using her, and us, as the standard for my relationships moving forward.

My friend Jessica* met a guy named Mike on 100hookup 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

Dear Tamar,

My former girlfriend is now on 100hookup, only three weeks after our breakup.  I still have feelings for her.  I have not put up my pic yet as I feel insecure about her seeing me on 100hookup.  I would like to contact her, but feel it is not appropriate as she is obviously seeking new men.  She will see me when my pic is put up. How do I handle this situation?

Dear Ex or Next?,

I don’t think 100hookup is the right forum in which to let your very recent ex-girlfriend know you still have feelings for her; that’s something that should be done in person or on the phone, not via a 100hookup email. If she had been an ex from long ago, I would say go for it as I think that’s romantic. But, since you just broke up, a different medium should be used. If you’re not ready to date then you should refrain from posting your pictures until you are emotionally available, otherwise it will be a waste of your time and the prospective date’s. Obviously, since you saw your ex’s profile is active, you know that she is trying to move on — even if she’s not ready, she’s trying to put herself out there and see what her options are. I recommend that to a lot of people as part of the breaking up and moving on process. On the flip side, you could post your photos, knowing she will see them and hope that any feelings she has for you will surface. But, hey, that’s playing games, both with her and your own heart and mind. Once the sting of knowing that your ex is ready to move on wears off then hopefully you’ll start being ready to, too. Good luck!