Q: Dear Holly. I’ve been lonely lately and thinking about an ex-girlfriend. I haven’t seen her in five years, but I wonder how she is. To be honest, I would die for another chance with her because I really fucked it up. I was drinking too much and never had any money. I’ve been working on things and think she would be impressed. Should I reach out, Facebook friend her, or try her old phone number. – Andrew
A: Hi Andrew. I want to touch on some of the specifics of your question. You say you’re lonely. It’s not unusual for men (and women) to think about exes when we’re lonely. It’s a very natural place to go, but it’s usually not a good idea to act on. Think of it in terms of moving backwards instead of forwards. If a relationship doesn’t work out the first time, it’s all but guaranteed to fail the second, or third time round.
You also say you haven’t seen her in five years. That’s five years wherein she could have contacted you if she wanted to. This reality is setting yourself up for disappointment. If you think you can handle zero response or a flat-out rejection, then go for it, but why not leave the past in the past and focus on meeting someone new. Assume that she is doing well without you.
Working on our issues is very important before getting into a relationship. Whether or not your ex would be impressed doesn’t matter. The only person you need to impress is yourself. Making positive changes in our lives has to be for ourselves first, always. When you go with this approach, the work works.
So, you probably see where I’m going with this. That’s right, I don’t recommend that you reach out, send a friend request or try calling her.
Stay on your path of self-improvement and look for someone new. Join an online dating site to find what you’re looking for, whether that’s casual hookups or something more serious. A few first dates with different women will help you feel less lonely, and who knows where they will lead!
I’ve been in your shoes, and every time I’ve tried to revisit old relationships, it’s been a disaster. Attempts to reconnect have not only failed, but it’s also had a negative effect on my self-esteem. Keep moving forward!
Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex, we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter.