So today’s SIDTA email, is actually geared more towards DATING, but I’m so stumped by this, I figured it was worth sharing.

Here is a dating conundrum that I can not figure out. I need to hear from the people of the world at large who have been through this and have practical pearls of wisdom to bestow.

Here’s the email:


Went to dinner the other night with a very close group of friends. We work together and our bond is not only personal, it’s professional. In this circle is a guy I have been close with for the last two years. I think (and have always thought) there is some sort of mutual attraction between us, but we’ve never acted on it!!

So back to dinner. We are eating, having a great time, when fate leaves the two of us alone. He declares how beautiful he finds me, then plants a kiss. He tells me he loves me and can’t even look me in the eye.

The kiss is where it stopped, but that kiss complicated everything! Since I know so much about his personal life, I know he has a history of screwing girls over. I actually saw it in action… several times. He seems to pull away anytime he gets close to someone.

And to make things even worse, when he declared his feelings, or attraction, or whatever, he followed that up immediately by saying that he was afraid that he would hurt me or let me down in some way. He’s also told me going on a date seems almost “too formal.”

Other than our friendship, our professional realtionship is at stake here…and so is our group of friends. What if it doesn’t work out?

I know that on occasion, people go from being friends to more than friends. BUT HOW?

I’ve never been in this position before. The closest I’ve come is when I accidentally hooked up with a guy friend of mine after a long night on Northgate. It was awful and we didn’t talk for YEARS.

But I think this is different? I am confused.

How does one go from being friends to being more than friends? Is it even worth it? Please advise!


Here’s where I’m stumped. My mind says, don’t do it!

Don’t let lust get in the way of your rational thinking. You’ve had a bad experience in the past with a friend, and this guy doesn’t even seem too eager to take you out.

Dates are too “formal?” It sounds like he’s not really making an effort towards bridging the gap between friendship and romance. Sure. I wasn’t around for his dramatic declaration of love, but his words alone seem too smooth not to be suspect.

And lastly, hello? He pretty much WARNED he was going to hurt you!

I guess there’s always the “what if”.. but I think past trends are a good indicator of future behavior. This guy sounds like a great friend but a !*&~^ boyfriend.

If it’s right, it should feel natural. If you’re stressing or trying to force something, it’s probably not.

Then again, I’ve never experienced this. Have you gone from friends to more than friends? Has it worked?!

What do you think?!