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The Follow-up, Second Date & Another Damn Breakup


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.

About Thomas Edwards

Thomas is a dating and lifestyle coach out of Boston and he helps men and women learn how to live more prosperous lives in hopes of finding self-fulfillment, love and satisfaction. He has decided to do a weekly segment called Ask a Wingman. Every week he will be answering your questions (with his tidbits) from the TSBMAG mailbags, so if you want your question answered, send them his way. [email protected]

Simple Trick Tells You if a Girl Wants You to Kiss Her

Do girls leave you confused as to whether or not they like you?

Let's face it.  Girl's don't make it easy for you.  She will often send mixed signals leaving you unable to tell if she is being friendly or flirty.  If you read her signals wrong you risk rejection and embarrassment. Or worse, you blow it with a girl who wanted to kiss you.

Here is a simple and innocent move that will instantly tell you if you're in the friend zone, or if she's waiting for you to kiss her.


  1. Hammer

    August 4, 2009 at 1:02 pm

    I love the advice to the guy with the breakup, but totally disagree with your texting theory. You need to talk to a girl on the phone ONCE to prove that you can, and after that it doesn’t really matter that much unless you’re trying to hypnotize her/escalate to phone sex.

    The real one that I need to assert my opinion in though is this dude with the fuck buddy going on vacation, because dude, that’s what you are to her. You’re a living sex toy. For many guys, that’s their fantasy, but it sounds like you’re catching feelings. The girl should be the one who’s trying to increase the commitment level in the relationship, and if she’s not, she’s probably not that into you.

    The point is, she expects you to be getting other ass, because I will men’s warehouse guarantee that she’s slobbing other knobs. Not doing so will leave you heartbroken and sexless.

  2. Kevin

    August 5, 2009 at 1:55 am

    Infinity, you weren’t too harsh with that last guy. You probably weren’t harsh enough.

    I really hate to see guys get hung up on a chick like that. I know guys like that and I just want to smack ’em around and give them a kick in the ass. There’s a huge world out there full of beautiful women. Get out there and meet some of them and have a good time!

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