Should I Let My Boyfriend Have Dinner With His Ex?

Dear Finding Hope,

I met Chad about six months ago through a friend and we have been dating every since. It  has been going really great. I don't know too much about his past, but I do know he dated a girl before me for about two years. She broke up with him but didn't really give a reason except she lives about two hours away from our town and she didn't like the distance and neither wanted to move. That's all I know. Anyway, last night he told me that she called and was going to be in town this weekend and wanted to meet him for dinner. He asked if I would mind. Well, yes, actually I do. But I don't want to look jealous or clingy. I don't know what her deal is and I'm hurt that he wants to go. What should I do? 

Signed, 

I Said He Could Go, But Not Happy

Dear Not Happy

That is a tough one for sure. It can be very frustrating not knowing what her goal is, especially since they dated for two years and you are not truly clear on what went down. You didn't mention if she knew you guys were dating.. When he brought it up, you could have said that the two of you could take her to dinner to see his reaction. If he is just being nice to an ex, he shouldn't mind if you were there. It is possible that she needs some closure, or she could be trying to find out if he has regrets and wants to try again. 

I would have felt better (and I'm sure you would have too), if he had told her no. It is a good sign that he asked your opinion as he could have tried to hide it from you. It doesn't really seem like he has an ulterior motive, especially if you guys have been getting along. I would suggest that instead of dinner, maybe they meet for coffee somewhere instead. They can still catch up, but it doesn't have quite that intimate feel to it. 

If he still insists on dinner, and decides to go, do your best to play it cool. Don't text constantly or check up on him. I think it is fair to know where they are going ahead of time and that he calls you when they are done. The bottom line is you can't really stop him, and the more trust you show, the better it will look for you. We cannot force anyone to stay and we certainly cannot force anyone to love us. They had two years to figure it out and couldn't. If he is a smart man, and you guys have a good thing going, he will recognize that and just have a quick meal, catch up a bit and come home to you!

Let me know how things go!

And always...

Hope With Abandon