They say that age is just a number. Well, whoever “they” is has clearly not been on many dates. There was a time when I was really frustrated dating guys in their 20s. None of them seem to have the attention span to keep a girlfriend. So I decided to give dating older guys a shot. And then I realized that they were just a little too old for me, a little too figured out. I would hear myself complain about it and I sounded like the Goldilocks of men’s ages. This one’s too old. This one’s too young. Does anyone have markers so I can make a sign saying, “Wanted: JUST RIGHT”?

I’ve even developed a test to measure a guy’s age to his maturity level. It started when I was on a sixth date with someone who was almost 9 years older than me. I liked everything about him. He was nice, smart, hard working, and our families had a lot in common, but I couldn’t put my finger on one thing. What did he do for fun? I finally asked him this very question and he without missing a beat goes, “I don’t really know.” How does a person not know what they do for fun? Seriously. And then I asked THE question. The most important question for me to determine just how much one can let loose, not give a damn, and just enjoy life.

Me: Okay… but when was the last time you had like a fun drunk karaoke night?
Him: (long, long pause) 1998.
Me: That was the last time you really had fun like that?
Him: (shrug) Yeah.

Do I even need to tell you that this was the last date? It wasn’t the karaoke thing that was the deal-breaker. It was the fact that it had been 14 years(!) since he had a let-your-hair-down-Facebook-picture-worthy night. FOURTEEN years! Titanic was still in theaters the last time he had fun. Britney Spears was still a virgin. There was no such thing as an iPhone. I had a Tama-freakin-gatchi. I mean, this was a long, long time ago. When was my last fun drunk karaoke night? Two weeks ago to the day. But I have fun nights where I find myself smiling as if I have a hanger stuck in my mouth pretty often. And that’s a requirement for any guy I date. I instantly knew it was time to reel in the gap and date guys closer to my own age, even if they might not be as ready for a relationship as I am. I want to find someone to grow up with, not grow into. That poor guy though. He will never know that he was just one Livin’ On a Prayer away from a Total Eclipse of The Heart.

Every time I discuss meeting girls online for first or second dates I always discuss the importance of doing something fun.

As many of you know by now, I always encourage a first date to be fun, unique, and entertaining.  On top of this, to fit in games whenever possible.

Women not only love games, but they provide a nice opportunity to flirt.

For this reason I suggest investing in a Nintendo® Wii or an Xbox® Kinect.  To this day I have never met a women who does not smile every time you bring these gaming systems up. 

You will not only have fun with your date, but they also provide you with a great excuse to invite your date upstairs to “hang out” for a little bit longer.  For most men, inviting a date upstairs can be awkward.  It is strange bringing a date inside, only to have nothing to do.

Having one of these systems gives you a reason every time.

100hookup profiles are really hard to mess up.  They’re also really hard to get right.  It seems that most of the profiles I have come across fall between these two extremes.  According to the 100hookup population, every hookup person on earth is easygoing, fun, loves friends, and loves to laugh.  Let’s examine these four characteristics.

First, I love easygoing people, but it’s getting a little cliché when people describe themselves as ‘easygoing.’  I think that being easygoing is a prerequisite for being on 100hookup.  Thus, there is no reason to describe oneself as such.  I already assume that you are easygoing because you are chatting with strangers and going out on dates with people whom you have never met in person.  Putting ‘easygoing’ in your profile makes it sound like you’re trying really hard to be easygoing, but are actually extremely demanding and tough to work with.  Easygoing people are way too cool to have to describe themselves in this way.  I would be really interested in a girl who claims to be inflexible and difficult in her profile.  I would take her out based on curiosity and on the fact that there’s no way she’s ever been on a date in her life.

Let’s move on to ‘fun’ people.  This word is similar in meaning to ‘easygoing’, and thus doesn’t need a very long analysis.  Again, people are going to assume that you’re fun, or else they wouldn’t talk or go out with you.  Unless you’re really hot.

Now we are at people who love their friends.  According to 100hookup, people love to go out of their way to say that they love their friends.  However, the word ‘friend’ itself implies that you have affection, otherwise you wouldn’t have friends.  Therefore, I think that it would be more correct to say, “I have friends.”  Actually, don’t say that either.  You’re trying too hard.  I know that you love your friends.

Finally, we have people who ‘love to laugh.’  This is the most confusing and troubling thing to say about yourself.  Who hates to laugh?  Really?  You do?  Then why are you laughing?  The act of laughing itself is a testament to the fact that you love to laugh.  Everybody loves to laugh.  Laughing is fun and great.  Again, if you hate to laugh, I would love to take you out just based purely on curiosity.