Ask Your Wingman

Today, I want to talk about the most important thing when it comes to maintaining your social life. The follow-up.

Although this requires effort (as most good things in life do), it’s a very simple way to keep friendships and opportunities abound. I shouldn’t really have to give you examples on this but just in case you’re not sure, I’ll give you one. One that is important to me.

Call your boys and hang out. For those of you who may have a girlfriend, it’s important that you don’t fall in the time-suck that can be your relationship. You need to make sure that you have your part of your life still together. That involves doing other things that DO NOT involve your girlfriend and the best thing to do is hang with your boys. You’ll love yourself for it, it’ll make your relationship stronger and I promise your lady will enjoy the space herself (so she can hang with her girls or just not be with you – it’s ok, it’s healthy). Plus, your boys will appreciate the time and not think that you sold them out to a girl. Guys do take this seriously, whether they say it or not.

This is way too important to ignore. Don’t forget the people that helped make you who you are. Hang with your boys. It’s fun, it’s manly and it’s healthy. Do it.

Let’s keep it short so we can go into the mailbag.

The other night, I went out with a girl. We had dinner and went to see a movie. We had a good time and we’re going to go out again but what would be a good idea for a second date? Should we do dinner again? She mentioned a place that she wanted to go to (I think it was the park or something). Maybe I could surprise her with taking here there? What about going in for the kiss? When should I do that?

I’ll be quick and to the point. Don’t take her the movies and don’t take her to dinner. Do something fun that will get the two of you talking and sharing with each other. It’ll be the best way to get to know each other.

As for the kiss? If you kissed her already, I’d kiss her as soon as you see her. If you haven’t kissed her, then I’d do it at any point prior to the date ending. There will be less pressure and if she’s receptive, you won’t have to worry about if she’s going to kiss you again at the end of the date – unless you’re a terrible kisser or have unbelievably disgusting breath.

So I met this girl at a party a few months ago. We ended up hooking up and I got her number. We kept in touch for a week and then when we got together we had a good time and hooked up again. Since then, things have been pretty much the same. I’ve never expressed anything that would make her think that it is serious. It’s been awesome.

Now she’s going on vacation for a couple of weeks. I asked her what’s going to happen with us. She responded by saying that she wasn’t sure and that we’ll see when she gets back. So what now? Did I mess up? Should I wait til she gets back and see what happens?

No, you didn’t screw yourself. I think it was good to ask since you were unsure and wanted to know. It was also important because you got an answer. She’s not sure. Regardless of her reasoning, you should decide something. If waiting for her is worth it? Questions I should be asking is if you are seeing anyone else and are you looking to commit to this one. But when it comes down to it, she’s only gone for two weeks. If you can afford to wait, then do so. Otherwise, see what else is out there in the meantime and if no one else stacks up and she wants more, then it’s all good. If she doesn’t want more, then it’s still all good because you’re not leaving yourself with little to no other options.