Gaining Confidence – Dating Tips for Shy Guys

Find your perfect match with these dating tips for shy guys. Boost your confidence, learn how to make conversation like a pro, and push your boundaries—learn more here!

Dating as an introvert can often feel like swimming upstream, where your reserved manner and preference for being alone (or at least with those you know well) seem to keep pushing against your ability to meet people. But just because you’re not as outgoing as another guy doesn’t mean that you can’t have a thriving dating life. 

These dating tips for shy guys can help you boost your confidence, pursue romantic opportunities, and overall become a more self-aware man.

Ditch the Idea that You Have to Make the First Move

Making the first move is rarely easy for anyone, but for introverts, it can be downright terrifying. Asking someone out involves several things that shy people try to avoid—but all at the same time—like initiating conversation, taking a risk, and putting themselves in the spotlight. So, do shy guys have to make the first move? It depends on the situation and how you’re feeling at the moment. 

Traditional dating often dictates that men make the first move, which can add a lot of pressure to dating for introverted guys. Rather than thinking about it in terms of “I have to,” think “I can.” This shift in perspective about who is supposed to ask whom out not only removes some stress but also gives you the power to determine if you’re ready emotionally and mentally. 

You don’t have to be the one to make a move. You can wait for women to take the lead or any person you’re interested in. Just be sure that you’re not using this perspective as a crutch to shield you from taking a chance. A healthy mix of asking someone out confidently and knowing when it’s okay to let them come to you is key.

Learn How to Carry On a Conversation Like a Pro

Lengthy conversation might not be your strong suit, but here’s a hot tip: One of the best ways to participate in a conversation with your date is to ask them questions. Most people enjoy talking about themselves, including their passions, travels, hobbies, and so on, so lean into that by asking them about all of these things. Our list of what to talk about on a date is a great starting point. 

But one of the top dating tips for shy guys is to remember that you don’t want the date to feel like an interview! To avoid this type of awkward date, (1) try to ask follow-up questions based on the topic of conversation rather than throwing out unrelated questions one after another, and (2) talk about yourself as well. A good conversation involves both listening and sharing.

Suggest a Date Somewhere You Feel Comfortable

One of the keys to a successful date as a shy guy is to be as comfortable as possible. Yes, going on a date with someone you’re still getting to know is nerve-racking, but make it easy on yourself in other areas, like your choice of clothing and where you go on a date. 

For example, if you’re not a fan of loud bars, suggest a quiet, intimate spot that you’re fond of. Or if you don’t want to feel pressured to converse the entire time, pose the idea of trying a new activity together, going to a museum, or seeing a show. Maintaining one aspect of the date that’s somewhat comfortable can make the nerves a little easier to handle.

Discover more date ideas for introverts.

Build Confidence in Other Social Settings

As an introvert, you’re probably no stranger to feeling uncomfortable in certain social settings. Some might be easier to navigate than others, but if you simply don’t feel confident socially, especially in situations that are romantically charged, it’s time to practice your social skills. This is one of the best dating tips for shy men to help build confidence.

Try participating in non-romantic activities that can help boost your confidence. Consider joining a local Toastmasters club, participating in group sports that you enjoy, or volunteering in group environments. Some of these ideas take place in settings that are ideal for perfecting your casual conversation skills, while others (like Toastmasters) are focused on getting comfy in front of large audiences, which can, in turn, help you to be confident in front of smaller ones.

Be Flirty

You don’t have to be an extrovert to know how to flirt. But it’s true that outward signs of interest might be harder for an introvert to display. Everyone flirts in their own way, but here are some flirting signals that are easy to show off: 

  • Sustaining eye contact or at least glancing at them continuously
  • Using flirty emojis in texts
  • Displaying flirty body language, like smiling, open arms, physical closeness, or light touches

Keep in mind that flirting only goes so far. Pair these flirting signals with your confident conversation skills for the ultimate dating tip for shy guys.

See Dating as an Opportunity, Not a Risk

Changing your perspective on dating can improve your outcome. Oftentimes, introverts view social activities, dating included, as something to fear or be preemptively exhausted by, which can make them cancel plans at the last minute or say no altogether. Though it’s completely normal to be nervous about an upcoming date or at the thought of asking someone out, think of the activity as only so many minutes of your life. The potential positive outcome far outweighs the romantic risk of putting yourself out there or learning how to deal with rejection

Give Yourself Space to Recharge

You might be super motivated to find your person, taking as many opportunities as possible to meet people and go on dates. That’s great! But one of our dating tips for shy guys is to prioritize your mental and emotional health. 

One of the main differences between dating for introverted guys vs. extroverted guys is that reserved men often need time to recharge between social activities. These moments are crucial for maintaining your balance of energy, emotional and mental processing, and even “letting down” physically. If you’ve ever noticed your body relaxing the moment you return to your car or your house after a social activity, that’s your cue that you might need some time to recharge. 

So what does this all mean in terms of your dating life? Make sure you give yourself space between dates to avoid burnout.

Try Not to Rely on Texting

It’s easy to default to texting when you’ve met someone online or in person. After all, for introverted guys, typing can be a lot easier than face-to-face interactions. But don’t fall into the text trap. After the initial text convos, get out of your comfort zone and ask the person on a physical date (or virtual date if long distance). This is the best way to find out if this person is for you.

Take a Different Dating Approach

If you haven’t found success with online dating, dating apps, or meeting people organically in your daily life, it might be time to try something new. Matchmaking services can not only save you time and effort, but they also have the ability to provide matches that are more aligned to your preferences and personality. Using a matchmaker can be immensely helpful for extroverts and introverts alike who might desire a more curated and intentional dating process.

Remember that Being Shy Isn’t Something to “Overcome”

If you only take away one of these dating tips for shy guys, we hope that it’s staying confident in who you are and the strengths you have to offer. There is a common misconception that introverted people need to learn how to talk more, be in the spotlight, and generally push themselves further onto the extrovert scale. Don’t internalize these opinions! While learning how to be more confident is always a good thing, stay true to yourself and remember that what you might lack in outgoingness, you make up for in listening, perception, and even empathy, all traits that your future partner will love. 

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