Random Q & A (Part X)

QUESTION: The guy I’m dating wants to know what my ‘number’ is. It’s a lot higher than his. Should I tell him or not? He told me he’s going to assume my ‘number’ is worse since I’m not telling him.


When it comes to the ‘number’ game, it can be a difficult process to discuss with your significant other. I actually had the same situation with my girlfriend when we began dating. Her number was significantly lower than mine because she had different morals/values than I did. She also intended on waiting until marriage. I had a different lifestyle in college before I met her and lived my life accordingly. When we came across this subject, it was a bit awkward to discuss. We both knew the type of lifestyle I used to lead, but she had no idea my number fairly high. That said, the best thing you can do is be honest with your partner. Everyone had their own lifestyles before meeting their significant other and should not be punished for what happened before you met.

There is a reason you may have engaged in sex with the other men. But at the same time, there is also a reason you are not dating them. Former boyfriends/girlfriends and one-night stands do happen. And it is not something anyone can take back. Yet if the guy you are dating truly cares about you, your ‘number’ shouldn’t cause him to turn away from you. By explaining things to him, hopefully it will make him trust you for being able to talk about such a difficult topic. And it will also help strengthen your relationship. When I did, my girlfriend respected that I could come clean, even though my ‘number’ was significantly higher than her. And I’m proud to say we are currently going on 3 years of being together.

QUESTION: There is a guy who is friends with my best friend and he lives an hour away. I can’t tell what he wants to do or if I’m just a fwb? He calls me a couple of times a month to see me and we have sex every time we see each other which makes it feel like we’re fwb. We’re not officially dating or anything, so we’re free to date other people.


You have to ask yourself a few questions. First, are you actively searching for a boyfriend or just playing the field? Second, are you developing feelings for this guy beyond sex? Third, what happens after you guys have sex? Do you continue to hang out in social settings such as going to the movies? Fourth, do you want to date him exclusively? Once you answer these questions, it will be easier to approach this situation.

If you are actively searching for a boyfriend, but you are continuously having sex with him when he visits, naturally you will develop relationship-type feelings. If you do hang out in social settings, then it’s no wonder why you have these feelings. If you answered yes to 2nd and 4th questions, then I suggest talking to him about your feelings. The worst thing you can do is to let things sit in your mind, letting it become jumbled and twisted.

Overthinking usually leads to disaster in relationships or before a relationship. You should speak what’s on your mind and heart. Then you can see where he is at. He might possibly be having the same type of feelings, but doesn’t want to rock the boat by asking you. It sounds stupid, but when it comes to stuff like this, some guys are really nervous. They are honestly just happy being in the situation they are in not wanting anything to happen asking the question, ‘what are we?’. If you feel this way and wish to pursue it as a relationship, just let him know how you feel. If he is on the same page, it should work out beautifully. If not, then you have to determine if fwb is the right thing for you and adjust accordingly.

QUESTION: I always meet assholes whenever I go to the bars/clubbing and end up dating them. I’m tired of it, how do I meet better guys? A good guy would be great, but those don’t seem to exist as often as the assholes.


I’ll be the first to tell you that assholes are EVERYWHERE! As a guy, I consistently see them with some amazing women. It makes me wonder how the heck they do it. Well I have an answer for that. The reason assholes continue to get great women is because great women continue to fall for asshole moves. We all know what they are and how they act. Most of the time, they all look the same. If you want to find a real man and not just any guy, meet them outside of the bar/clubs. Here’s how it usually breaks down by the numbers for guys at the bar/club: 70% are assholes, 15% happily married (their wife is with them), 10% have girlfriends and are committed, and 5% are single and are good guys.

When any of my friends tell me, ‘Oh we met at a bar’, I think to myself, ‘another one bites the dust’. I know it’s hard to hear. But meeting people in a bar and having it work out is like hitting the lottery. It is VERY rare. Most people at the bar usually have two things on their mind, 1) how fast can I get drunk and 2) who is my target to hook up with? My advice to you is try your best to just go to the bar with friends to simply have a good time. Don’t focus on trying to meet guys there with the notion of starting a relationship. I understand you have no control of where you meet someone, but a bar is usually a difficult spot to find a great guy. Try doing activities that you enjoy like such as sports/social clubs/gym. The chances of you meeting a great guy at these places and having it turn into a healthy relationship is vastly higher than if you try it in a bar.


Faithful to DC


I was recently at a bar and a girl approached me to hook me up with her friend. The friend started talking to my friend. And she and I looked at each other puzzled. I ended up talking to a cougar most of the night, so that’s all I heard from the ‘wingwoman’. I don’t approach girls in bars as that’s not my thing. Later on in the parking lot, I ran into the wingwoman again and the horny, drunk guy in me took over. I gave her my number, I gave her a kiss and asked her where the after party was. She looked at me strangely and I got a sense that hooking up on the first night was not her thing. She told me, ‘I’m going home’ and we’ll talk tomorrow. I messaged her later asking her to come over to my house an hour away but she was firm. She said we could meet up tomorrow and I agreed. I passed out and that was the end of the night. The next day she messaged me and we started planning to meet up. I told her I was moving back to DC and was only here for a month and a half for a work gig as a flight instructor. She pointed out I didn’t mention that last night and well, I didn’t want to because I didn’t want to ruin my chances with her. But now I was sober and being the good guy I am, I was honest about that. We agreed that we should have some fun before I left. She was a cool, down to earth girl, and neither one of us really did this kinda thing. So, it seemed exciting and we started trying to make plans. I told her that she couldn’t come over because I had coworkers as roommates. Coming over after they sleep wasn’t an option as one was still out that night. I didn’t tell her it was really because my roommates knew the girl I was dating before I left DC. I planned to be with her when I came back, so I didn’t want to ruin my chances. She lived with her parents so that wasn’t an option. We talked about outdoors on the beach but I didn’t want to go to jail. I had to work the next day so we agreed to meet the next day. The next day we talked, she mentioned her friend offered her place up for her to use during work hours. That wouldn’t work because I didn’t get off work in time. I had some time the next day, so I rearranged my schedule and made some time for her. Now I’m having second thoughts and not sure if I go through with this. I will practically have a girlfriend when I get back to DC. Should I take advantage of this opportunity? Am I making a mistake if I don’t? I feel like I’m cheating, am I?


Am I really getting a question from a guy on whether he should hit it or not? This would be a first. It does sound quite exciting and a once in a lifetime kinda opportunity. The kind that’s similar to the feeling of sex in a foreign country or vacation, because that’s really what it is if you’re just visiting there in such a short time. But, we all aren’t built to just listen to our loins all the time. And although you’re not officially with the girl in DC, you might as well be with the guilty conscience you have. There is such a thing as being faithful nowadays and I applaud you for being cognizant enough to take your time deciding. There’s 2 ways to look at this, 1) you’ll have your fun but with time, your memory of it will eventually fade, is it worth it? Two is, do you want this to become the sort of behavior and lifestyle you want to adopt for yourself? First experiences are fun, but they don’t always end at the first time. You are in a sense opening Pandora’s box. Should you do this one time and you know you have the girl in DC, what’s gonna stop you next time when she is your girlfriend? Titles are just that, titles. If your heart is with someone, title or not, your heart is still with them. And that sounds like what the case is now. You won’t bring her around your roommates, so obviously, part of you is concerned more about your future girl than with you living in the moment. And frankly, when life hands us so many challenges to obtaining something, it’s usually a sign that we probably shouldn’t have that. I think I counted like at least 5 hurdles to the execution of your fling. You’re on the right road questioning it, now make your decision final on where you’re headed on that road and close this out. Besides, who knows, the sex may be a flop and disappointment. Who ever wants that? Tighten up your boot straps and hold that desire in. You’ll be seeing that future girlfriend soon enough and you can have that celebratory coming home sex marathon! Now, that, I’m sure will not disappoint you. So, go forward with anticipation of your next chapter, be proud of yourself that you say not to the cotton candy in your hand that so many would’ve not denied, and good luck to you in DC. Next time, when you are (which I’m sure you will have a girlfriend) go to a bar, you may want to be careful of both getting that drunk or even getting a girl’s number. Either and both of these wouldn’t have put you in such a dilemma to fail.

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