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How to Date Shy Guys: Your Complete Guide

Posted Sep 24 2014 - 2:00pm
Tagged With: shy guys

It’s hard enough trying to figure out what any guy is thinking, but it’s even more difficult to read a shy guy. When you fall for a shy campus cutie, it may not seem easy to figure out if he likes you back.

Some guys are just inherently shy, says Geoffrey Greif, a professor at the University of Maryland School of Social Work and author of Buddy System: Understanding Male Friendships. He adds that young women need to “understand that some shyness is embedded in the guy... and some shyness is contextual, i.e. certain situations or groups.” No matter the reason behind your guy’s shyness, our love experts can help you figure out how to make him yours! 

How to Get His Attention

Greif, Jasbina Ahluwalia, founder and CEO of successful matchmaking service Intersections Match, and psychotherapist Mary Waldon all agree that the number one tip for trying to date a shy guy is to take initiative! Whether this means initiating eye contact, a conversation or a date, all of our experts stressed the importance of taking that first step.

When you spot a cute guy across the room and think he might shy, Ahluwalia advises collegiettes to give their shy guy a “green light” by smiling or holding eye contact for a few seconds. This makes it easier for that interested but shy guy to approach you. Unlike more outgoing guys, shy guys might need a confidence-boosting signal from you to give him the courage to make a move.

Even if the shy guy doesn’t return your gaze, Ahluwalia says it doesn’t mean he doesn’t like you. She assures collegiettes: “Many men are more comfortable side-to-side with another person than facing the other person directly,” she says.

Greif adds that while women like face-to-face activities, “men hang out with their friends through shoulder-to-shoulder activities.” If you show interest from afar but your guy is still too shy to approach you, then the next step is to go up and talk to him!

How to Chat Him Up

After you walk over and make that initial contact, Ahluwalia says that “providing a warm and inviting opening” is the best way to help a shy guy engage you in conversation. “Don't worry if you continue to be more [talkative] than him as you develop your relationship,” she says. “Complementary personalities can be a great match.”

If you have difficulty being outgoing as well, Greif assures collegiettes that that’s totally normal. “Be okay with a little bit of silence,” he says. “People who are getting to know each other may not know how much silence to allow [because] silence can be uncomfortable if it goes on for too long... but talking too much can shut down quiet people, too.” If all else fails, you can always get a shy guy to talk by asking him a question. You probably shouldn’t quiz him on his opinion of the meaning of life, but asking about his favorite sports team can be a great opener.

How to Ask Him Out

If you’re already friends with the shy guy you like, Greif tells collegiettes that while you should be comfortable with initiating a date, you shouldn’t rush things. “Moving from a platonic to a romantic relationship can take time and the ability to read the situation,” he says. This is especially true of shy guys who may guard their emotions more than their more outspoken friends. Waldon agrees that you should take it slow and suggests “low-key interactions such as a daytime study date or tutoring session.” It can be difficult for a shy guy to ask out a girl on an official date, so asking your shy guy to casually hang out clues him in on your interest so he can feel confident to take your interaction to the next level.

Greif says that another great way to get to know a shy guy is to participate in activities that interest you both. “See what the commonalities are between you and the guy,” he says. Greif cautions collegiettes not to get involved in activities that only he likes; he says, “You have to like them too. Finding mutually enjoyable things to do is one way to get to know someone.” Waldon agrees and suggests that you “invite him to a social service or volunteering event that you enjoy— this is something important and meaningful to do and it will give you something to discuss, too.” When your guy is comfortable in his environment or sees you comfortable in yours, the interaction between the two of you will come naturally and easily.

How to Make Him Fall for You

Once you’ve had a few low-key interactions with your shy guy, you and he will both feel comfortable enough for you to invite him to an outing, like a concert or game night, with a small group of friends. Because it’s a group event rather than a one-on-one date, this is a low-pressure way for you to get closer to a shy guy. Once again, you help take the pressure off him because you’re the one who initiated the interaction.

 

Greif adds that although this will make many shy guys comfortable, “some guys who appear shy are very interested in getting to know people and may feel more comfortable with a quiet talk/one-on-one situation.” A shy guy’s affection may not be obvious, but even the most bashful boy will show his interest with someone who makes him feel comfortable. Although it may take more time for a shy guy to open up, if you follow this guide, he’ll be yours before you know it.

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