How To Make The Most Of A Relationship With A Shy Guy

It’s a fact of life: almost everyone gets nervous when it comes to dating—even guys! Opening up and sharing some raw, powerful emotions can turn even the most confident guys into a shrinking violet. And, in addition to sharing their feelings, many guys get self-conscious about putting their best foot forward and making a good first impression. This shyness can be endearing; I mean, it’s flattering to have a guy care about impressing you so much that he gets a little flustered. But, on the flipside, it can be frustrating when it impacts how the relationship progresses. 

We all know how hard it can be to read shy guys. Their reticence and introspectiveness can sometimes come across as a lack of interest when in reality, they are crazy about you. So, how exactly do you get a shy guy to open up? More importantly, how can you tell if a shy guy is in to you? And, when you finally do score a date, how do you make it memorable and not awkward?

Well, rest easy ladies; here is everything you need to know about getting a shy guy to come out of his shell. 

So…does he like me, or not? 

Flirting, as fun as it is, can be confusing as heck. And if you are anything like me, nine times out of ten, you leave the situation having no idea that a guy was flirting with you. This dilemma becomes even more confusing when you are talking to a shy guy. 

Fear not, there are some cues that shy guys will give that could indicate that they are interested in you. 

Jasbina Ahluwalia, a relationship expert and matchmaker, and the founder of Intersections Match by Jasbina, says that shy guys typically offer physical cues when they are interested in a woman.

“You might catch him looking at you,” Ahluwalia says. “[He might be] preening, perhaps running his hands through his hair, or attempting to decrease the physical distance between the two of you.”

If you are picking up on these signs, it might be up to you to make the first move. In this situation, you want to strike the right balance between being yourself, but also making sure the guy you are talking to is comfortable. Ahluwalia recommends being approachable, but also making an attempt to engage the guy you are interested in. 

“Give a sincere compliment, smile warmly, then ask for help: in a store, you can say, ‘Great tie—I like your style. I’m buying a tie for my brother’s graduation. Which of these two do you think works better?’” says Ahluwalia. 

Initiating a conversation in a casual way is a fantastic way to get a guy talking with you!

Related: How To Tell Someone You Like Them In A Non-Awkward Way

Choosing the right date

Once you’ve established your mutual interest, the next hurdle to jump is the date itself. A classic, traditional dinner date can seem intimidating (lots of conversation can be a little much for shy folks), so what are your options? 

Ahluwalia suggests finding an active date that incorporates something you and the guy are interested in. 

“[Choose] any place where he is in his element and can shine! An activity date can take the pressure off face-to-face conversation and let him shine as the two of you interact.” 

Examples of these activity dates could include going to a wine-tasting, taking in a musical event, going to a farmer’s market, or attending an art opening. 

Megan Mann, a Purdue graduate, had success matching her guy’s interests.

“My ex-boyfriend was really shy,” Megan says. “What I found to work out was finding out what his interests were and catering to them until he opened up. Once he was comfortable, it was much easier.” 

If you aren’t looking for something super active, try a twist on a classic date idea. Typically, movie dates get knocked for not giving couples enough time to talk, especially when the goal of a date is to get to know the other person! But, a movie date can be perfect for a shy guy. You all can chat before the movie starts, and then just sit back and relax as the movie plays. Afterwards, you all can grab coffee or a quick bite to eat, and instead of scrambling to find conversation topics, you can just discuss the movie! You can talk about what you all loved, or debate things you felt differently about. And, learning about their taste in movies (among other things) can spark further conversation, and hopefully, even more date nights! 

What do you do on the date? 

Once you have selected your date night activity, you actually have to go on the date! And even when you’re tasting wine or critiquing art, there are some small things you can do to keep conversation flowing and your guy at ease. 

“Compliment him genuinely, share enthusiastically about yourself and actively listen when he does talk,” says Ahluwalia. 

She also recommends asking open-ended questions that could help him open up more. 

Daniela Reyes, a senior at the University of Illinois, has had this work for her. 

“I usually try to drive the conversation to get it rolling since it usually does not seem like they would start it or continue it,” Daniela says. “Then, I try to find something that they like so they can get comfortable with talking. Even asking about what they are wearing, a class, work, the weather, or something can get the conversation going.” 

How can you tell if the evening is making your guy uncomfortable? The answer is once again in his body language! 

“[If] he increases the personal space between the two of you, closes his arms, frowns or averts eye contact,” Ahluwalia says these could all be signs that he might not be enjoying the evening. 

But what if you’re also shy? 

Birds of a feather flock together, so it’s no surprise that shy girls might be attracted to shy guys. However, this mutual shyness can result in two people (who are really into each other) sitting in awkward silence for an hour and a half. So, how do you cross this divide of timidity? 

“Someone has to get outside [their] comfort zone, and initiate the conversation—let it be you,” says Ahluwalia. “If you’re a bit nervous or shy, feel free to be vulnerable and share that—it could be a point of connection. Guys appreciate heartfelt vulnerability.” 

Emily Schmidt, a Standford sophomore and self-described introvert, has recently been faced with this problem. 

“I recently started dating an extremely shy guy, and as an introvert myself, I thought I wouldn’t have much trouble making him feel comfortable around me,” she says. “However, I discovered that it takes a lot of time for shy guys to open up, especially if they weren’t friends with you before the relationship.” 

If you yourself are shy, it’s important to remember that your guy is feeling the exact same way you are: excited, but kind of scared and not sure what to do about it. In this case, it’s best to practice the golden rule (yes, the one from Kindergarten) and treat others the way you want to be treated. So, be positive, kind, and, most importantly, yourself, and both you and your guy will feel comfortable in no time!

Related: 6 Dating Tips for Shy Girls

What matters most in relationships is that you connect with someone and feel comfortable sharing with them. And, as frustrating as it may be, sometimes this just takes time. 

“I didn’t want to scare him off because I really liked him, so I let him make all of the moves," says Schmidt. "He didn’t kiss me until about a month of hanging out, and even then, it took him an entire movie plus five minutes of credits to work up the courage. You have to be really patient and accepting when it comes to making a shy guy feel comfortable.” 

And you know what they say—sometimes the best things in life are worth waiting for.