15 Tips for Dating a Shy Guy ...

15 Tips for Dating a Shy Guy ...
By Kati • Sep 16, 2025

You’ve found the perfect man, flirted to perfection and now you have a date. Sounds perfect, so what’s the problem? He’s shy! Shy guys might be cute and endearing, but on a date, it can lead to awkward silences and tension. There are ways to cope with this shyness, though! Here are my top ten tips for dating a shy guy.

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1. Spend Time as Friends

Shy men are often loud and confident with their friends, but find girlfriends intimidating and can’t help getting shy! Spend time together doing friend things, and not only will you get to know him but he’ll learn to drop his guard, too.

2. Talk to Him

Ask him questions. Tell him about your day. Talk about your pets, your family, your favourite place. Talking to him will encourage him to open up, without feeling like he is being interrogated. Do most of the talking, but let him talk, and ask questions.

3. Read His Body Language

If he isn’t saying how he feels, look for it. Does he look like he wants to speak; is he making continuous eye contact, does he look bored? What he is doing will usually portray what he is thinking, so read it carefully. It’s your secret weapon!

4. Remember Things

Commit important details to memory. The name of his mum, his favourite colour, the name of his dog... it’ll make you feel more involved in the conversation if you know exactly who he is referring too, and he’ll feel like he’s known you forever.

***

Remembering little facts about him not only shows that you care, but also helps in creating a deeper connection. When you recall specifics that he's shared during previous conversations, it sends a signal that he has your full attention. It's things like asking how his mother's new gardening project is going or mentioning his favorite sports team's latest game that can brightly light up his day. These small acts of remembrance can go a long way in nurturing a relationship, especially with someone who tends to be reserved or shy.

If you're looking to engage your partner in intriguing conversations, why not try some hypothetical questions for couples? These fun queries will not only keep the conversation lively but also stimulate deep thoughts and potentially reveal insights about each other's personality and thought processes.

5. Tell Him about You

Talk about yourself. Show him you can be trusted by telling him your secrets, and all the little details about you. He’ll feel more comfortable when he knows who you are, and you’ll soon be rid of a shy guy and have your own confident hero!

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6. Be Careful with What He Tells You

If he confides in you, however small, keep it to yourself. While it might feel good telling a few close friends, and you’ll be thrilled at getting him to open up, if you violate his trust he’ll never trust you again.

7. Arrange Dates

Arrange dates with him, so you won’t be waiting for him to get the confidence to call and arrange a second. Try going to the cinema, so he doesn’t have to talk so much, and save picnics and that sort of thing for when he’s opened up a little more.

8. Be Encouraging

Look at him while he is talking, and pay full attention to what he has to say. Shy guys find it hard to talk already, so if you make him feel like what he is saying is worthless, he’ll get even quieter. Make eye contact, and avoid distractions like your cell phone.

9. Introduce Him to Family and Friends Carefully

Take your time with this, and think about it. Keep loud people to last, and anyone who is likely to make jokes. Warn the people beforehand that he is shy, and ask them to be nice. Most people have felt shy, and will immediately understand!

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10. Flirt

Just because he is shy, doesn’t mean you shouldn’t look good. Be confident, happy and flirty, and show him exactly why you are worth the effort. You won’t regret it! There’s nothing that brings a shy guy out of his shell more than a flirty girl.

***

Flirting with a shy guy calls for a mix of subtlety and boldness. Lean in when you talk to him, touch his arm gently to emphasize a point, and don’t forget to flash those dazzling smiles his way. However, always be mindful of his comfort zone. While some teasing can be fun, pushing him too hard might backfire. A light-hearted and playful approach can spark his interest and encourage him to open up, proving that behind that shy exterior lies someone who is just as interested in the thrill of a flirtatious exchange.

11. Understand His Nervousness

Of course, dating a shy guy can get really frustrating sometimes, but you’ve got to make sure that you understand his nervousness and some of the behavioral acts that he has. If he doesn’t immediately make plans with you, don’t take it personal, it’s because he’s nervous!

12. Don’t Pressure Him

Pressure is just going to put your shy guy right back into his shell, so make sure that you don’t pressure him to be someone he isn’t. If you are dating him, you are most likely dating him for him, not because of how confident he is. Remember that!

13. Figure out His Comfort Zone

Just like he has to figure out your comfort zone, you’ve got to figure out his comfort zone too! That means that you’ve got to work at finding out what makes your shy man tick and where he is most comfortable. Give it a try and see how easy it is to date a shy guy!

14. Make Him Feel as Comfortable as Possible

Making him comfortable should be something that should be a high priority, after all, he is the shy one and you are the outgoing one. Make sure that the things you do aren’t outside of his comfort zone and are things that you both like to do.

15. It’s Worth the Investment, Remember That

Finally, while it might be harder to date someone that is a little shier than you, it is worth the investment! Shy guys are beautiful people and they are oh-so-sweet, so remember, when you are dating a shy guy, it’s worth the extra time it takes to coax him out of his shell!

Once he’s out of his shell, he’ll be more confident than shy, and you’ll have a dream relationship! Just remember that shyness is a natural defense, and be nice. He is trying! Have you got a tip on dating a shy guy? Please share it with me!

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Where Thoughts and Opinions Converge

the rest of it wont copy and paste :(

as a guy I'm quite confused by this positive talk about shy guys. Why are we constantly being told how important confidence is for attracting women?

^^ thanks for the information i gonna try it to my crush.. . coz he is shy, im gonna get his attention seriously.. .! i will not give up.. ^^ .. . . i will write soon if what is the result.. ^^

I am one these shy guys you talk about. I am not a shy as I once was but the key for me anyway is I am shy at first because I like to feel someone out. See what is ok and how far I can go. It is important I feel comfortable before I let someone in. As mentioned trust is key.

Help!!!! This is a long story, but I really need some advice! About a month ago, I left my number with this guy who plays piano at a dueling piano bar. I have a friend who went to high school with him, but they weren't friends. She said he seems really nice, but was very shy and awkward, except for when he performed. I left my number, and then three days later he texted me. We talked for a while and I broke the ice by asking him what he felt when I left a note and my number for him. He took a long time to respond, but ultimately said he was really happy and thought I was the hottest girl in my group of friends. From there, we arranged to hangout that Friday. His band was playing at a mall, so he invited me to hang out with him after and watch the concert if I wanted to. I went, and we met up afterwards. He was very awkward at first, I almost considered just going home from the mall to go to bed, but my friend convinced me to stick it out. We drove separate cars from the mall to where the bar was, and met there. My friend came along too as support. He ended up being much better because he was in his element. We hit it off, and I ended up going home with him and we hooked up. From then on, we hung out 5 more times with in 8 days before I had to leave the city. We slept together twice more in those 5 times. We stayed in touch over the next week and a half, and then I made an effort to drive back and see him again. We had a great time too.... but here is the problem: He is moving in a week or so too, but farther away from where I am moving to. I feel like because we didn't talk about what we wanted out of this, it inevitably became pretty casual because we have assumed nothing can last because of the long distance. Yet, I feel myself really liking him, but finding it hard to read him at times. He is a pretty bad texter, but started to use a lot of smiley faces after we warmed up to each other. I'll ask him questions, but he is not good at keeping the conversation alive. When he does ask me a question, I am quite surprised! When we are together, he definitely shows signs that he likes me. It is always a little awkward, but in a good way. We warm up eventually, and we'll hold hands, kiss, etc. I've gone to work with him before, and I definitely catch him staring and then looking away when I stare back. He even showed a bit of jealousy that time towards the end of the night when he was at the bar drinking water, and I was sitting by myself at the table. Then this other guy started harmlessly talking to me. When I walked towards my guy at the bar because he sort of gestured me over, he made a comment: I see you're making new friends! I could tell he was jealous because immediately he grabbed my hand, even though we hadn't touched the whole night since we were warming back up to each other. Silence is comfortable for us, we watch TV together and eat. We do these girlfriend/boyfriend-ish things, but there is still this cloud looming! I wanted to talk to him about it the next day (yesterday) before I left again, but he overslept and then we didn't end up seeing each other because he had a busy day and I had to leave for a road trip. I did text him being like: so, I'm guessing you don't have time for a quick goodbye? And he said :( I'm sorry I don't think so... I let it go and texted him byee. Is it worth trying to talk to him about it? Or does he just want this to be casual because he is moving in a week? He is confident at weird times, but definitely comes from a place of having been very closed off/shy/and still a bit awkward. I feel so secure and warm inside when I am with him, but the shy side of me also feels I am the only one feeling this way. What should I do? I told him I was going to come back next weekend and see him play one last time at the bar and with his band. Just let it be a summer fling? I'm so torn because I can't tell what he is thinking :( Sorry this was so long. It has been quite a saga and crazy month for me. Shy guys are so tough!!!!

hey :) im in the process of getting to know this shy guy. im a junior and hes a senior. for a while ive had a crush on him, but i didnt feel it so strongly until i had a dream about him and i somehow going out, which was a couple months ago. me and him are (very-ish) shy people, but in some situations are very confident and relaxed. on valentines day, i confessed to him that i liked him, and he told me that he felt the same way, and that hed love to get to know me better and try something more if i was up to it, and of course i was! since then, we had midwinter break, and we texted when we could (hes really bad at texting, even more so with our complicated schedules, but a lot better at talking in person). he more recently started using little hearts here and there in his texts. towards the beginning of this week he texted me and he called me babe

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