7 Tips for Dating a Shy Guy

A girl who's dating a shy guy, smiling as her boyfriend grins next to her with his head on her shoulder.

Social anxiety is often hard to conquer. It can range from someone not being able to muster up the courage to say hello to a stranger, to someone having a full-blown anxiety attack before giving a presentation. There are a number of reasons why someone could be shy, like being afraid of saying the wrong thing or not being very self-confident. Although many adults can power through those feelings, they can still exhibit feelings of shyness.

If you like a guy who happens to be on the more timid or reserved side, don’t use that as an excuse to downplay his potential as a romantic partner. Once a shy guy starts getting comfortable with you, he can be a phenomenal boyfriend.

To help the shy guy you’re dating feel more relaxed in your presence, follow these seven tips:

Start out slow.
Don’t bombard a shy guy with a ton of details about yourself right away—you could come off as a little intimidating. Also, don’t monopolize the discussion. Try to get him to participate in the conversation with simple tidbits. Stuff like, “The weather’s amazing outside, right?” is a lot less scary than, “So how many kids do you want to have someday?”

Know that you need to build trust.
When you’re first starting to date your new man, provide a safe environment and perform actions that’ll prove to him that he can trust you. Once you develop that trust, it’ll be a lot easier for him to start opening up to you. However, make sure you don’t break that bond. For example, if he shares a secret about his family, don’t blab about it to your girlfriends. It’d break his heart if he knows he’s immediately the center of gossip and could make him even more closed-off.

Don’t make fun of his shyness.
Social anxiety is a real struggle that he’s trying to overcome. Making a mockery of it, or having a big discussion about it in a public place, isn’t okay. Accept him for who he is, especially since there’s always a possibility his social anxiety is from a past traumatic experience. If you like him, but can’t get over the initial shy barrier, he might not be the one. But just remember, the situation can get better with a little bit of practice and positivity.

Try to think up some fun, creative questions for him to answer.
Ditch the serious talk, and start up a conversation with a question based on entertainment. What’s the one book he’d take with him to a deserted island? What was the worst movie he’s ever seen in theaters? These require a little bit of thought, so he won’t feel like he’s put on the spot. As a bonus, you’ll be able to learn a little about his hobbies and interests, as well.

Consider going to the movies for a first date.
While grabbing drinks is all the rage, a movie is a wonderful first date idea too. You’ll get to spend a few hours together without the pressure of having to carry a long conversation. By the time the movie ends, you’ve shared an experience (and some popcorn) that you can both chat about. Even if it was a terrible movie, you can still talk or laugh about it. Remember, the key here is making sure he’s comfortable.

Be upfront about splitting the cost and other date details.
When you have a date planned with a shy guy, it’s possible he’s sitting at home worrying about all the things that might go wrong. This could make him even more reserved during the night. Take initiative and try to prevent this before it even begins. Be friendly and open up about some of the date elements up front. Saying, “I’d love to split the cost of this with you,” will help relieve any anxiety when the bill comes. Also, having a game plan for the whole evening could take a lot of stress off his shoulders as well. If you think it might be fun to grab ice cream after dinner, make sure you tell him that from the start. Dating won’t always be so formulaic, but starting out that way could help him ease into his comfort zone.

Make sure to be a good listener.
If he opens up, it’s a big step forward for him. Make sure you do your best to actually hear what he’s saying, ask relevant follow-up questions, and stop yourself from talking over him or interrupting. Listen to what he has to say, engage in it, and learn from it. This is an important skill to have and it’ll help you become a more attentive person in other areas of your life too.

Shy guys might assume that their timidness might turn people away, so it’s extra important to make sure they know they’re valued.

Karen Belz

Freelance Writer

Karen Belz has written for sites like Bustle, PreviouslyTV, Heavy, and HelloGiggles. She’s also the founder of Best Recap Ever, a site that’s focused on television news and reviews. She’s a fan of sketch comedy shows and most movies that involve Muppets, and has been addicted to Sugar Free Red Bull since 2005.

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