Ask Your Wingman

We are going to continue to talk about dating, relationships and maintenance this week. Some of you had some interesting feedback on my responses and I love it when people get into the conversation. This week shouldn’t be any different.

Let’s hit the mailbag.

Hey Thomas,

I’m pretty young so bear with me here. I was with a girl for over 5 years when we were in high school. Everything was amazing – almost too good to be true. We even went as far to making plans for the future (AKA marriage, living together, etc.). It was really like I was living a dream. Then over the course of a few weeks, she allowed her friends to convince her that we were too young for such a commitment and she ended things.

It wasn’t the end of the world really and I decided to let her go. To try to get over her I busied myself with working and school. I fell off the radar completely. But still with all of that going on, I thought about her everyday. I even decided to take on more activities in order to get over her but it’s not working. The whole situation was fucked up and I know I’m still in love with her. I miss her so much.

Socially, I went from being the man, to pretty much not being a man. I have been on dates, but none of them compare to her and I just don’t have enough interest in them. I was hoping that if I hook up with some women, it would help me get over her. Nope.

There was one time when she was drunk and she texted me saying how much she misses me and that she thinks about me all the time. She wants us to be friends as she tries to find herself but I can’t have that. I’ll only want more and because we can’t have that, I’ll go crazy. I just don’t know what else to do. It’s fucking my life up.

First of all, how shitty is it that your girlfriend let her friends decide what was best for her? It almost seemed like she had no voice in the decision. It also seemed like there wasn’t much talk about it, which is also shitty. I guess she didn’t respect you or the 5-year relationship enough to try to talk things through with you and hung you out to dry. Yup, pretty shitty.

You don’t need that in your life and as much as it was unfair to you and as much as you are still in love with her, you HAVE to move on. If it means hooking up with anything that breathes then so be it. Distracting yourself with activities only works for short-term results. You are just prolonging the inevitable. You’re not moving on – you’re just running away from your emotions. It’s ok to feel the way you do. You got screwed.

She clearly misses you and doesn’t know what she’s doing right now and that’s the last thing you need right now. It’ll just make things worse. Stay away from her at all costs for right now and focus on yourself.

What you have to do is stop comparing other women to her and find someone that you can build something new with. This girl had to have been your first everything considering how old you two are but you have to refrain from comparison. It’ll only set you up for failure. And if you open yourself up to more options, you may find someone who’s worth your interest.

Go out, have fun, make new friends, meet new people, build a life for yourself and go on some dates. Doing work, getting into activities and going to school is all good and fun but it’s only half of moving on. Hope this helps.

So I’ve been seeing this girl for a while and we like sports and activities. We are supposed to play basketball one-on-one. We always talk about who would win and we’re both pretty competitive. She used to play in college but I seriously think I’d win because she’s little and I’m so much bigger than her.

Should I let her win? What if I actually tried and she still beat me? Would that be bad? What if I tried and I beat her? Would I be an ass for not letting her win?

It’s funny I look at this because my girlfriend and I were talking about something similar. I have no idea if she’s any good but I would never treat her like I’m going one-on-one with LeBron James. I think it’s fair to be competitive and visibly try to win. I don’t agree with destroying her in what should be a fun game of one-on-one. If you try and she beats you, it’s whatever. I just wouldn’t let that leak to your boys.

If you let her win, she will know and she won’t like you for that. If you annihilate her, she’ll be pissed, unmotivated and that won’t look good for you. Just go out, have fun and be competitive.

Look on the bright side, this gives you an excuse to make her back you down in the paint.