Ex now jealous?

Dear Sleepless in School,

Juggling romance, exes, friendships, etc. can indeed be a tricky endeavor. It seems like gaining a better understanding of what you want may be a good place to start. Understanding what you want out of a relationship will help you figure out which relationships are worth pursuing and how you may handle any consequences that may result from those decisions. 

First, you mention that you still have some feelings for your ex. What kind of feelings and how strong are they? It seems as though you want him in your life in some capacity. Would you be satisfied just being friends with him? Would you feel okay if the two of you were less than friends? Is saving his feelings (assuming he is jealous and doesn't want you to date other people) more of a priority to you than dating the person you met at the party? It may be somewhat difficult to casually date two people who are friends with each other. How would you feel if dating the new guy meant eliminating your ex as a dating option, at least for now? You're clear about liking this other guy and wanting to see where things could go with him. Having that same level of clarity about your ex, if possible, may be helpful.

There's also the question about the friendship between the new person you met and your ex along with the accompanying pressure to not date the new person. You've noted that it doesn't seem fair to not date this new person. That feeling perhaps stems from two places. First, your ex broke up with you initially and when he wanted to get back together, you both agreed to date other people. Second, their friendship with each other isn't your responsibility. It seems as though pursuing this relationship with the new person fits within the agreements you and your ex made.

The issue your friends may be overlooking in their advice to you is that you aren't the only one making decisions about whether or not to date this new person: He gets to decide if dating you is right for him, too. He may or may not be weighing the factor of your ex — his friend — in his decision-making, but it does indeed seem unfair to place the responsibility of their friendship on you. Their friendship is really up to them to figure out, just like your friendship with your ex is between the two of you to sort out.

When two people break up, it's often painful when an ex starts dating a new person. One or both people may feel jealous, sad, angry, confused, or a myriad of other emotions. If you're worried about hurting him, you may choose to communicate with him compassionately without sacrificing your desire to date this new person (or other new people in the future) that he may be acquainted with.

In the end, it's your call whether or not to pursue this new dating possibility and if so, how and what to communicate to him and to your ex. These questions have no easy answers, but trying to get some clarity about what you want and then trusting your gut to show you the course of action for you may be your best bet.

All the best,