How do I overcome being shy to start a relationship?

I am an intensely shy person who is smitten with anther intensely shy person. We occasionally will do things together but I simply cannot initiate the forging of a connection with this girl. What should I do? I don’t relish the prospect of giving up, so I don’t consider that an option.

Don’t give up! We went through something similar. It worked out. Eventually. Though maybe that says mixed things about our credentials for answering this question.

It’s a bit unclear what you’re looking for. Are you just hoping to spend a little more time with her, aiming to get your relationship to be emotionally closer, trying to get her in bed, or looking to start an official relationship?

Regardless, we’ve got some ideas. Of course, the most straightforward and effective thing you could do might be to just tell her how you feel. But we understand if you’re having trouble with that.

So we’d recommend you focus on tangible things you’d like to be different about your relationship. If you’d like to spend more time with her, try to spend more time with her. If you’d like to have more personal conversations with her, start more personal conversations with her. If you’d like to cuddle with her, maybe start by doing something fairly unobjectionable like giving her a hug or back massage and gauging her response.

But maybe even those things are too hard. So here are a few more specific ideas. If you want to spend more time with her, consider stopping by her room before meals to see if she wants to go with you, joining/starting a club you’re both interested in, or inviting her to do fun things, like going to the movies or a campus event, going for a walk, or baking something together.

Or if you want your relationship to get more personal, suggest games/activities that encourage people to talk about themselves, like taking the purity test together (puritytest.org). And if you need a reason to be more physically affectionate, say you’re trying to improve your massage technique and want someone to practice on. But try not to get too creepily manipulative about it all.

Having mutual friends can also be helpful. They’d give you reasons to hang out more with her and find out more about her, and they could be helpful (but also horribly annoying) if they figure out you like her.

Recommendations: A couple of general books about sex and relationships in college.