Got a Shy Guy? Help Him Relax with These Surefire Tips

Key Points

  • Dating a shy guy means taking the lead: in making the first move, sex, and more.

  • While it might seem difficult, dating a shy guy has some specific benefits.

  • You may have to rethink your current ideas about dating to make the shy guy in your life feel comfortable.

Dating a shy guy differs from what you’re normally used to. The majority of men are afraid to talk to women for fear of rejection. Even confident men get nervous when approaching a potential lover.

A shy guy, though, takes being nervous to a whole new level. Shy people tend to be introverted: They keep to themselves and enjoy solitary interests or prefer pets over people. It doesn’t mean they're socially inept or don’t enjoy company; they’re just deeply uncomfortable making the first move.

Dating a shy guy is not without its challenges in the beginning. But shy men can make great partners once you get to know them. The trick is making them comfortable enough with you to open up.

Tips To Make a Shy Guy Comfortable While Dating

You've got a crush on the strong, silent type. He won't make eye contact with you, but you've got to get his number. And once you've started dating, how do you keep a shy dude feeling relaxed?

Read on for tips to make a shy guy comfortable while dating.

1. Make the First Move

A shy guy isn’t the most confident on the dating scene. If you’re interested in an introvert, don’t expect him to make the first move. Dating and social activities are not a shy guy’s best subjects. He spends much of his time alone and, thus, is not the best conversation starter. He may want nothing more than to ask you out on a date, but he’s terrified of what you’ll say. He may even be so terrified of dating you that he hardly acts interested. In his mind, it’s never going to happen.

If you want to move forward with the shy guy and have any chance of having a relationship with him, make the first move. Though typically, men are expected to start the chase in a relationship, many men love when women make the first move. They respect when a woman is confident to take matters into her own hands and declare her interest. It’s less guesswork and does away with the chance of being rejected.

In a shy guy’s case, this isn't just hot — it's necessary. The introvert will likely never have the courage to ask you out, so be prepared to make the first move.

woman touching man's legs under table with her feet

2. Take the Lead In Planning Dates

The shy guy has little experience wooing women with grand date ideas. When dating a shy guy, you must take the lead when planning dates. Leaving it up to him will put him under pressure he might not be able to withstand. He'll be terrified of picking the wrong restaurant, choosing the wrong gift, or not wearing the appropriate clothing.

He may also not have a great idea of what is hip or fashionable. Many introverted types aren’t necessarily into what's trendy. They spend more time on their studies or solo interests than on fashion. They don’t know what the rest of the world is into, so what might be an exciting date idea to him could be a total drag for you.

Tell him what you want. Drop obvious hints about a new restaurant you want to try or mention a part of your city you’d like to explore. Give him apparent clues as to what you want him to do. Communication is essential in any relationship, but perhaps even more so when dating a shy guy. He likely has no problem doing whatever you want, but he needs help knowing what you want to do.

There's something pretty endearing about wanting to impress you so much, right?

3. Be Direct With Your Feelings

Most men have difficulties deciphering how a potential partner feels about them. A shy guy has even more trouble figuring you out. Remember: A shy guy doesn’t have much experience with trials of the heart. He’s unsure what signs to look for that signal a girl is into him. You may be batting your eyelashes and laughing at every one of his jokes, but he likely has no clue this means you like him. He’s not confident with himself and his social abilities, so he will have difficulty believing you like him.

If he doesn’t call as often as you’d like, it could be because he's afraid he's bothering you. He doesn’t want to come off as aggressive or weird. He’s more afraid of upsetting you than taking the chance that you do. If you're interested in a shy guy, tell him! Don’t expect him to pick up on your body language; you need to be more direct. Tell him you enjoy spending time with him and want to continue.

Tell a shy guy you're interested; you will get nowhere with him if you don't.

Woman Kisses Shy Man

4. Lead the Conversation

Shy guys are not the best in social situations. They may be awkward in conversation because they're not used to talking with a person they're attracted to.

Expect awkward silence when you first get to know him. You'll also likely need to be the conversation starter to get him talking. A shy dude won’t be great at small talk, so take the lead. Find a common interest that will be easy for him to discuss. Asking questions is a great conversation tactic because it gets the ball rolling. People feel more confident in answering questions about themselves or their life because it’s a subject they know best.

Shy people rarely start the conversation but become more comfortable when you keep it going. Don’t be afraid to lead the way and talk about various subjects. A shy guy may not be the best conversationalist, but he’s likely a good listener. He’ll love to hear what you say — especially if it means he can stay quiet.

5. Build Up His Confidence

Having a shy boyfriend means you'll need to build up his confidence. The dating scene is not his forte, and he'll be unsure of every step he takes. Help him build his confidence by reassuring him that he's doing an excellent job. Tell him how much you enjoyed the flowers he picked for you or how much you loved the meaningful conversation you had the other night. Compliment him on the shirt he wore to your last date, or find another specific detail to focus on.

While the compliments and attention might initially make him uncomfortable, he'll slowly begin to realize his worth. Building up someone’s confidence is a beautiful thing to see. You'll watch his personality change from a shy introvert to a beaming, affectionate partner. When you build up someone’s confidence, you watch them reach their full potential. They become the best version of themselves and will have you to thank for it.

When you help a shy guy build up his confidence, he'll fall in love with you even more. Building a man up is one surefire way to get him obsessed with you. 

Shy woman and man sitting close to each other on couch.

6. Be Patient

Getting a shy person to open up to you doesn’t happen overnight. It can be incredibly frustrating doing all the work and putting in overtime on your part trying to get a shy guy out of his shell. But introverted people take their time getting to know people. Your shy guy is not used to letting others in; no matter how hard you try, he will go at his own pace. It can be hard waiting for him to open up.

You might mistake his hesitancy as disinterest, but that’s likely untrue. Introverted men are not as comfortable laying their feelings out on the table. He may care for you but is unsure how to express his feelings. He may also want to take his time for fear of you breaking his heart. Again, a shy guy doesn’t have much relationship experience and may do less for fear of being clingy. If you want to date a shy guy, you must understand that it will take a while before he can open up to you.

7. Initiate Intimacy

There's nothing that makes a shy guy more nervous than physical intimacy. Of course, he dreamed about it but never dared to act on his urges. Don’t be surprised if the shy guy you want to date has limited sexual experience. The idea of actual sex may be a foreign concept to him. Although he wants nothing more than to be intimate with you, he's unsure how to initiate it. His biggest fear will be putting a move on you that gets rejected. He'd be mortified if that happened. It likely causes him so much anxiety that he will never have the courage to make the first move.

Once again, the burden to act falls on you.

Make it obvious when you want to get intimate with a shy guy, but no that there is no rush. Give him time to warm up to you, then go for it. Your best bet is to make non-aggressive first-time moves. Cuddle up to him when you’re watching a movie by taking his hand or laying your head on his shoulder. Innocent gestures like this will be undeniable signals that you’re into him. He’ll feel more confident knowing you want to be near him.

When the time comes, flash him the googly eyes and lean in for the kiss. It might be an awkward first kiss, but it’s a start that will only lead to more intense sexual connection in the future.

african american couple, woman kissing man's cheek

8. Give Him Space

Introverts recharge from spending more time alone, while extroverts gain energy from being around others. If you’re an extrovert, it may be challenging to understand why your shy boy needs alone time. It’s nothing personal, but sometimes a shy guy wants to do things alone. He needs his space to recharge. It doesn’t mean he doesn’t enjoy your company; it just means he can’t be around people 24/7 without feeling drained.

Not every single moment must be filled with doing something together. Give him space to step back and relax independently with his hobbies. He will appreciate you more for it. He will resent you if you force him to constantly pay attention to you. He'll associate being around you with being exhaustive and may rethink your relationship. If you don’t want to push him away, let him have his alone time to take a breather.

You could use that solo time, too! 

Smiling teenagers looking at each other sitting on bench, acquaintance moment

9. Don’t Pressure Him

A shy guy needs time to adjust to your lifestyle — and the lifestyle of coupledom. Don’t pressure him to partake in social situations or events he’s uncomfortable with. Remember that shy individuals feel anxiety in social settings — especially at large social gatherings. Take your time introducing him to your friends and family. Introverts do better one-on-one, so don’t invite him to a huge family gathering (lest you want him sweating through his shirt and blurting out something inappropriate over granny's peach cobbler) until he has met people individually.

The same goes for taking him to parties with your friends. A shy guy is not into the party scene. He prefers a quiet night at home to a loud, crowded environment. Forcing him to party with you isn’t his idea of fun and will make him wish he was anywhere but there.

To introduce him to your friends, invite them for a quiet dinner. Meet up with your friends for a coffee date, somewhere you all can have a quiet conversation so he can get to know your friends properly. Pressuring him to fit into your lifestyle will only backfire. He’ll more likely retreat into himself or avoid being around you.

The Benefits of Dating A Shy Guy

It seems evident that hooking up with an introvert is rife with challenges. But there are many specific benefits to coupling with a shy dude, too:

He Doesn’t Have an Ego

A shy guy is not as likely to have an exhausting ego. You won’t catch yourself eye-rolling at his self-serving monologues.

A shy guy will never feel like he needs to compete with you. He’ll be happy to let you take the spotlight and love watching you shine. For him, letting you be the center of attention makes him happy. It keeps the attention off of him and lets him enjoy a social scene without feeling pressured.

Young african american man in red sweater isolated on blue studio background peeping through fingers, hiding cover face with hands, looking terrified

He Doesn’t Use Social Media

You won’t have any issues with a shy guy misbehaving on social media. A shy guy is not your typical male. He’s not into trends and probably isn’t into social media. He most likely doesn’t have a social media account, and if he does, he uses it seldom. A shy guy won’t be flirting with other hotties on Instagram because that’s not his style. He doesn’t crave validation like most guys do.

He Doesn’t Party

If you’ve been with a man who likes to party, you know the headache that can be. You won’t have to worry about your shy boyfriend misbehaving while out with friends. The party lifestyle is not his idea of fun. He won’t be out late drinking at bars around temptation. And if he does go out, you won’t need to worry about him ignoring your texts or calls.

Being a player is not in a shy guy’s interest. He doesn’t base his worth on how many girls he can pick up in a night. A shy guy is more likely to be faithful than any other type.

He’s a Great Listener

Introverted personalities are more introspective and observant. They prefer to listen and watch rather than be the center of attention. Because of this, they often make great listeners. Expect your shy boyfriend to be an excellent person to talk to when dealing with important matters. He's more interested in listening to your problems than putting in his two cents. He'll take the time to listen to what you have to say and respond accordingly. A shy guy won't waste your time with meaningless conversation.

Take the Lead and Get Shy

Are you dating a shy guy or interested in dating one? Shy guys make great partners if you understand their personalities. They take time to open up, but you can help them by being supportive. Be patient and take your time with your shy guy. A rewarding relationship is just around the corner.

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