Pal Rider

I've been friends with this guy for almost five years. We've always been attracted to each other, but we've never been single at the same time. Now we're starting to date, and I have to say I feel a lot more safety and trust because we were friends first. I'm also not as concerned that he'll take me for a ride or play games. Am I being unrealistically optimistic, or is there some truth to this?

--Been Hurt Before

There is safety in having been friends with a person for a while, like how you can be reasonably sure that when he says "Here, let me help you into the car," it won't be the trunk. And because we evolved to care deeply about maintaining our reputation, it also helps that you two have mutual friends. (A bank robber is less likely to hit a branch where all the tellers know him by name.) However, once you're in a relationship, all sorts of emotional issues can pop up and start biting, and what prevents that is not having been friends but having done the work to fix whatever was bent or broken. To be realistically optimistic, make yourself look at the guy's worst qualities, and decide whether you can live with them. You should also consider what went wrong in your prior relationships. Sure, getting hurt is sometimes a random act, like a stove falling out of the sky onto your car. But often, it's something you could have seen coming -- and would have, if you hadn't been so busy sewing all the red flags into a big quilt. Finally, even if a guy doesn't have a skull in his kitchen cabinet labeled "Marcy," keep in mind that there are special surprises that will only reveal themselves once you're "more than friends" -- like his superhero underwear and his habit of taking over a bed "alphabet-style" (warding off zombies by sleeping in the letter X).