After two years, he wants me back

Hi Meredith,

I dated Jimmy for only a few months and we were friends for a bit before. In our friendship and relationship we always got along well and had a lot of fun. We were crazy for each other, or so I thought. During our relationship he was struggling with depression, money, family issues, finding work, etc. I was there for him and even helped him find a job.

He met someone at work who gave him her number. The next day he broke up with me. We didn't talk for about two years. Fast forward to today and we've started talking again. He caught me up on everything that happened in those two years and it was a lot, to say the least. But he's in a better situation than before, having a job in his field, saving money, and paying off school loans. He has spoken to a therapist to help with his depression and family issues and found a good circle of friends. He confessed he still loves me and was so stupid to let the best thing in his life walk away. He's taken responsibility for all his actions and wrong doings and apologized for everything. He wants another chance.

When we were together he would talk about marriage and our future. But let's not forget he ended it. I still have feelings but I'm not sure if I should try again. I'm scared of history repeating itself. Any advice?

– Confused, Boston

I'm stuck on the fact that you only dated Jimmy for a few months. In that short time, you managed to fall in love, talk about marriage, and experience epic heartbreak. Jimmy sounds intense. That's not always a good thing.

You're more than welcome to try it again with Jimmy (you obviously want to), but please keep him in perspective. In many ways, you barely know him. You'd just be dating him to find out whether he has any potential. There shouldn't be talk of love and marriage. Keep it simple, at least for now.

Also, you wrote a lot about Jimmy in your letter, but told us very little about yourself. And it seems that when you reunited with Jimmy, all you did was talk about his issues. Perhaps that's just how you framed it, but I'm concerned that Jimmy only cares about Jimmy. You're just as important. If you don't feel like a main character in this story, please bail.

My gut tells me that Jimmy is temporary, but I understand why you want to try. Just pay attention and remember that he's just a guy who walked away after a few months. This second chance doesn't have to be so monumental.

Readers? Does Jimmy deserve another shot? Is he important? What's happening here? Help.

– Meredith