Can You Date If …

Chatter Commencing.

I’ve dated my fair share of people. For the most part, they all started in generally the same fashion. I met the girl. We flirted. I got her number. We went out. If we hit it off, we continued dating. I would guess that most people have experienced this general relationship path before. However, there are a variety of situations that arise where, like a flower growing in the sidewalk, a relationship grows in an unlikely place. Each must be handled delicately. But if you keep your manners and communicate, you can build a lasting foundation, even on the slipperiest of slopes. So, without any more delay, I’d like to present my favorite game, Can you date if  __ ??? Let’s dive in boys and girls. Remember, I’m writing from my POV, so feel free to replace pronouns with your personal favorites, and also remember that this is generalized for mass consumption.

As a way of shedding light, I’m also going to be using some good old Friends references to explain certain situations.

Can you date if … she’s your friend’s sister?

This is one of the most over-used examples in television. Ross originally is distraught at the idea of Chandler and Monica dating, but comes around after they tell him it’s not just “fooling around.” The morale of Ross’ reaction is simple. If you’re going to date a friend’s sister, you gotta let him know ahead of time and/or that it’s more than just a fling. If you really like her, and she you, there should be no issue. Although, I highly suggest keeping the snogging to a minimum in front of him. (P.S. If anyone could draw the image of Ron nodding his head in approval of Harry & Ginny’s Kiss (Book Version), in say, 3 short comic pages, I would love you to death).

Can you date if … you work together?

I detail this particular issue in my “Company Ink” article, but I will say it again here. NO. Do not do it. It’s very tempting. It seems like the best idea. It sucks. The aftermath of an office romance creates crazy drama that no one really wants to deal with. So save yourself the time. Avoid the work fling.

On the other hand… the office fling is one of the hottest you’ll experience. The constant work flirt gets you revved up all day long, and when the end of the day rolls around, all hell breaks loose. My final conclusion? If it’s Elisha Cuthbert, I think the juice would be worth the squeeze.

Can you date if … she is 4 years younger than you? 

I picked a random number here. I figured it didn’t matter where I started, but simply the rule I’ve learned and followed over the last half decade. It’s a little different than the commonly thought of Age/2 +7, I choose instead to add 9. Thus, when you start at 18, you can date another 18 year old. It keeps things a little tighter on the higher end, as well. Everyone has their own standards, but for example, if you’re 24, and you want to date some, she should be 21 (12+9).

Honestly though, if you really like the person, you can work past age. It really is just a pair of numbers. And remember, “Your age doesn’t define your maturity.”

Can you date if … she’s dated one of your friends?

Yes. With only one condition. Ask First. Seriously, it’s the easiest thing in the world. I’ve actually been asked before. They asked me together, saying that they were interested in hanging out, but didn’t want it to be weird. I said it was totally fine, and they dated for several years. However, I’ve seen the same type of situation blow up. After my buddy Matt broke up with his on again/off again girlfriend, his roommate Craig, started dating the same girl. Craig was trying to find the right way of telling Matt, but unfortunately, word got back to Matt via other sources, and the two guys had a major falling out. The two are still not friends to this day. It is very sad. They were like two peas in a pod. So, ask and then enjoy.

Can you date if … she’s dated more than one of your friends?

This is an interesting example. And if you’re involved in a tight group of mixed friends, the odds are that over the years, you’ll be intimate with different ones. For example, the friends crew has had mixed histories. Every single “Friend” has kissed every other friend, and a variety of them fooled around together. It’s inevitable. So if you think she’s worth your time, and you both feel that way, go for it.

Can you date if … she’s the town bicycle?

Of course. Aren’t all men the town bicycle, willing to give anyone a ride? Just because she can and does take advantage of that same thing, doesn’t mean anything. More power to her.

Can you date if … she met you while still dating her old boyfriend?

This is by far the hardest one for me to write about, because it happens more often than you think. See the Matt/Craig situation. The aforementioned female and Craig never hooked up before the relationship with Matt was over, but because it happened so quickly, it left Craig a bit nervous about her ability to commit. Their relationship was constantly strained and eventually it broke off.

The media has always said that, once a cheater, always a cheater. It is about will and mental fortitude. If she gave in to you when she was weak, what will stop her from giving in to someone else when the two of you are experiencing minor turbulence? Tread lightly on this one. That’s all I must say.

Last one.

Can you date if … you were best friends? Yes. Yes, a million times yes. The road blocks for this one are pretty obvious. You both need to be single. You both need to be ready for someone. And you both need to find the other attractive. But the tricky part of this relationship is starting it. It’s very high risk, very high reward, and for some people it’s too risky. However, if you can get the timing right, you’re likely never to date again.

Now, my situations have been generalized, so please don’t barrage me saying that your situation is different and that I’m an idiot. Love works in really weird ways, so if you’re with someone wonderful, forget about how you met and focus on how that person makes you feel when you’re together.

Unless it’s your sister.

Closing Chatter.