He’s shy; will he ask me out?

Dear Guys,

So, this guy in my grade, J, used to be my best friend in elementary school. Like best friends. When high school hit, we kind of faded apart. Although we’ve always had this vibe (a good one) through high school, even though he had a girlfriend. (He always gave me looks.)

We’re both juniors now and he just broke up with his girlfriend, He contacted me and we talked a little. He invited me to his wrestling match. I went; it was awesome; we took a picture together. How do I know if he’ll start something, or get it rolling? I like him, but I don’t know if I should ask him out. I’d like to save myself from embarrassment. Because this happens a lot to me, I try too hard, and it ends badly. I like this guy, he’s kinda shy.

What do I do?!


Dear Isabel,

Thanks for your question.

We know you want immediate answers but you need to be patient. It’s a great sign that he contacted you and invited you to his wrestling match. But remember, he just broke up with his girlfriend and he’s probably dealing with the gamut emotions that accompany a split, both his and hers.

We can see you have a lot of passion for life, and that you get excited when you see a possibility. However, in your case, it sounds like excitement leads to impulsivity, which eventually leads to embarrassment. We suggest you take a deep breath, count to ten—or maybe 10,000!—and let him lead. He needs to be the one to take the initiative here. If he does, then you’ll have a good sense that he’s interested in you. If you do, then you’ll never really know how he feels, because guys will sometimes say yes out of boredom or guilt.

We hope it works out for you. Keep us posted by leaving a comment. And feel free to ask follow-up questions. Use the comments section below. (You must be Logged In to do so.)


ps. Please tell your friends about us. Thanks! (And check out our e-reports to read some useful information about the seven most frequently asked questions.)

Read More Relationship Advice and Dating Advice about high school dating.



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