“Help: I’m crushing on someone shy and afraid to ask them out”

Dear Sarah,

I have been crushing on this guy for about five months. We are both in our early 20s and attending graduate school. I knew as soon as I met him that he was someone I would like to get to know. The more I got to know him, the more I liked him. We have hung out together one-on-one multiple times and even when we are with other friends, it ends up just being me and him in a totally separate conversation that lasts long past when everyone heads home. He tells the best stories, talks mostly in movie quotes, and has eyes that I could drown in.

The problem is that he has never had a girlfriend or even been on a real date. I have talked to his friends about it and they love the idea of us together but divulged that he is afraid not going to be good enough for any girl. I am old fashioned and don’t want to ask him out, but I have been dropping hints for months. Everyone around us has figured out how I feel except for him. I love our friendship and it would be okay if he doesn’t want to change things. I really think he is oblivious and hasn’t taken the hint. How do I clue him in without making things awkward and losing him for good?

—Friendzone in Texas

Dear Friendzone,

Make your move, girl! What are you waiting for? He sounds dreamy. His friends have given you the green light and explained that he is not confident about dating. If he’s chronically girl-shy you need to get over being “old fashioned” and propel yourself into 2016, a wonderful time when its perfectly OK and normal for women to ask men out. Your one-on-ones haven’t worked, your late night chat sessions haven’t worked, your ladylike hints haven’t worked, the moment has come to be bold.

If he’s a guy in his 20s who has never had a girlfriend before, trust me, he’s going to need you to take the lead in way harder and more awkward stuff than initiating a first date, so you had better accept that if you want to be with him. He’s not going to magically transform into some kind of Mr. Swag. Be honest with yourself, do you like him just as he is, even if that’s bit quirky or out of step with his peers? If the answer is yes, you can lead with, “I really value our friendship and this might be awkward….” He may be suuuuuper relieved that you made a move.  Somehow I don’t think he’s simply “oblivious.”

On the other hand, if you secretly want him to be someone who he is not (experienced, confident, a manly man) then look for a beau elsewhere. It’s not fair to your friend to start dating and then expect him to change.

Love, Sarah

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