I am on my freshman’s year in college and I met this awesome guy with whom I could have endless conversations and we were alike in so many ways I couldn’t help but sort of falling in love with him. For some reason he decided to quit college and go do something else, after only two months of us having first met. We still chat online very often and have long, deep conversations and right then I feel like I could tell him everything, about how I feel yet I’m afraid. I’m afraid because I have absolutely no idea how he feels about me.

I can say for sure that he lacks a good deal of self-esteem. He’s one of those guys in whom most girls see nothing of attractive (obviously because they fail to look inside). He’s confessed that he suffered real bad heartbreaks in the past and that has never had a girlfriend, to start with.

Now, me, not to sound full of myself (I’m actually not at all) but well, I am a photographic model and know from feedback that my looks are above average. And believe it or not, this is one of the reasons why I think he feels like there will never be a chance for the two of us. Because he thinks he’s worse than me, because he thinks I’m too good for him, that I’d never really notice a guy like him… and ironically, he’s indeed the one that I like! But you can tell his insecurity around girls. He sits at least five feet away from them, he doesn’t compliment them, he doesn’t even shake hands or kiss to say goodbye.

How could I let him know he is special without being too obvious or sounding desperate? Is it okay for a girl to make the first move and show him she’s interested?

Jessica

Dear Jessica,

I’ll cut right to the chase: guys who are painfully shy at first usually step up to the plate once they realize that you are interested! The myth how a woman shouldn’t make the first move is outdated and too passive for a modern woman to accept. Plus, guys that appear dorky or insecure on the surface often end up real sweethearts with a lot to offer! So if your love interest is too shy around girls, the ball is in your court, literally – so grow a pair and ask him out already!!! :-D

As for being physically more attractive than your partner. You may have noticed that supermodels rarely date supermodels. Being in the superficial industry, they know what it’s like to be the target of one-dimensional appreciation and know to look beyond mere appearance. It sounds like you are intuitively doing it already.

Think of your guy as a diamond in the rough. Once the debris of insecurity have been brushed away and his self-esteem polished by your TLC, you’ll have a sparkling young man on your arm!

Deerlings: have you ever made the first move? How did it work out?

Got a question for Doe Deere? Get in touch at doedeere @ gmail.com.