I love writing about relationships, love, romance, and flirting. I hope you find the advice in my articles useful.
Dating a shy and introverted guy can be challenging because a girl will need to take the lead and make the first move. However, it can also be a blissful, enriching and pleasurable experience once a woman learns how to make him comfortable around her. Intellectual conversations, unlimited sweet romantic moments, cute expressions and honest body language are some of the things we will use to get him out of his shell.
1. Don't Expect a Shy Guy to Make All the Plans
Even if you manage to get a shy guy to like you and score a date with him, don't expect him to take the lead by making all the plans. A shy guy will lean on you and ask you where you would prefer to go as opposed to an extrovert who will suggest a great place for a date.
Take the initiative and suggest a place if you have something in mind. Feel free to give him suggestions about quirky date ideas because this is your chance to do something really romantic and interesting at the same time with a guy who is likely to be intellectually inclined.
2. Tell a Shy Guy That He Can Pick You Up
Instead of telling you the time at which he will pick you up from your doorstep, a shy guy could ask you whether you want to be picked up or you want to meet somewhere in the middle. A guy who is an introvert may even look at it as being practical and logical, as opposed to being a gentleman and offering to pick you up.
Don't take this the wrong way. A shy guy just isn't wired that way. Instead, suggest to him that he can pick you up if he likes. This will put him to ease because he may not be too comfortable being upfront about coming to your house to pick you up.
3. Give him a confidence booster before you both go on a date
It is a good idea to give your shy guy a confidence booster before you actually go on the date. This will help in removing the nervous energy and reduce the awkwardness.
For example, you can just send him a text message that you are really looking forward for the date. Or you could send him a private message on Facebook to show your excitement for the date.
4. Don't announce your dating plans on Facebook
Guys who are shy and introverts are not really the best at keeping up with social anxiety. You may be excited at snapping up a date with the cute guy but remember that he may not fancy the idea of five other people knowing about your date. It will put undue pressure on him.
Avoid announcing your dating plans on Facebook, Twitter or any other social networking platform. Any unnecessary comments may even put the shy guy off from going on the date.
5. Don't wear revealing clothes that make you look hot
You would generally want to look your prettiest and hottest when you go out on a date with a guy. But that is not the best thing to do when you are going on a date with a guy. He may be intimated by how gorgeous you look. This will make him feel extremely nervous and jittery.
A shy guy will not be able to handle the pressure of sitting with a drop-dead gorgeous girl. Avoid short skirts, hot pants, tops with plunging necklines or barely there outfits. Put him to ease by wearing jeans and t-shirt on your first date or jeans and a nice top if you want to look a tad more formal.
6. Complement a shy guy for his looks when you meet him
You can instantly put a shy guy to ease by giving him a compliment. Stroke his ego and don't mince your words as you compliment him on his looks or personality.
Don't play the waiting game to see if he compliments you first. A shy guy may be bowled over by how beautiful you look but he may just not have the courage to say it. He will open up slowly once you start.
7. Take the responsibility of starting conversations on your first date until he opens up
You will have to shoulder the responsibility of starting conversations with a shy and introvert guy on your first date. Men who are shy generally have a lot of things in their mind but don't know how to express themselves to women easily.
You will have to wait until your second date or till the time you develop a certain level of comfort with him. You will be amazed at the variety and depth of conversations that you can have with a shy guy once you get him to open up to you.
8. Bring out his inner flirt: Making a shy guy speak his mind
A shy guy will not even flirt with you because he could be nervous about offending you. He is likely to be afraid and will not want to take the risk of being the first one to start flirting.
The solution to this deadlock is simpler than you think. Ask him questions that subtly force him to flirt with you. Below are a few examples.
- So, do you like my dress? What do you like most about it?
- What is the first thing that you notice in me?
- Would you like to know why I find you good looking?
- I didn't know what to wear today so I wore my favorite jeans and top. I hope you like what I am wearing, do you?
Questions like these will make him a shy guy feel more comfortable about flirting with you on a date. He will no longer have to take the risk of being the first one to say something playful.
9. Build intimacy verbally: Make a shy guy comfortable with you on a personal level
Shy and introvert guys are generally truthful, non-manipulative, intellectual, cute, romantic and very well behaved. They have everything going for them except an ability to have their way with words.
Remember that a shy guy may not be used to talking about personal stuff with a girl. If you really think that he is worth building a meaningful relationship with, take the platform of your conversation to a personal level by sharing stuff that he generally does not expect other girls to say to him. Here are a few examples of how you can build verbal intimacy.
- I relax on the weekend by getting myself a glass of wine and watching a movie on my iPad while lying in a bubble bath. Everyone has a personal favorite way to de-stress, what's yours?
- I put my pink socks in the same load as my whites. Now all my white underwear is pink. Have you ever goofed up like that?
- I like hitting the bed early even if I am not feeling sleepy. I love to daydream. What do you like to dream about?
- I like wearing men's perfume, especially the musky fragrances. Which type of fragrances do you wear?
10. Don't get touchy feely on the first date, but do get touchy feely later
It may be common for you to put your hand on a guy's thigh as you laugh away at his jokes. But doing this with a shy guy could really freak him out. It can make him nervous and moves like these can give him wrong signals.
So stay away from getting touchy feely on the first date unless you strike an exceptional bond with him straight away. Observe some of his body language signs of attraction and use your hands once you feel that the both of you are comfortable with each other.
Put your hand on his shoulder, lean on to him in a friendly way while waiting for cab, give him a high five, tug his cheeks in a playful manner or hug him after your date. Hold on to your hug for half a few seconds longer than usual so that he feels comfortable with the physical closeness.
11. Don't Expect a Shy Guy to Kiss You on the First Date: Lean in Slightly to Give Him a Hint
How should I kiss her? What will my kiss feel like? What if she pushes me away? What if she doesn't like my kiss? A shy guy is probably shaking from his knees trying to figure out whether he should kiss you or not.
If you think that you want to seal the date off with a tender kiss, lean in towards him to give him a hint. Put your hand on his shoulder to make sure that he gets the hint. This move will make him a lot more confident about kissing you.
12. Send Him a Flirty Text Message Saying That You Enjoyed the Date
It is in an introvert's personality to analyze and introspect social situations, including a date. He may be fretting about how the date went on his way back home. Send him a flirty text message and put him to ease by telling him that you really enjoyed the date. Here are some examples.
- Today was really fun. We should do this again sometime, and really soon.
- I wish our date could have been much longer. I really enjoyed it.
- Thanks for showing me a wonderful time. I will have a lot to dream about tonight. ;)
- This was one of the best dates I have had. It feels as if I have known you since ages.
- I really love our deep conversations and hope that we can meet again soon.
Kristina on February 18, 2020:
Well. I am on the other side of the spectrum, extrovert, daring, and a girl. honestly i feel trapped due to liking very shy boy. mentally it hurts, i did all i could for him, still he moves forward like a turtle! I wish i could grab him right to my bed or vanish him entirely from my mind.
Dudes, dear shy dudes, for god sake if you do not like someone, go away like you never ever been. If you like someone then let her take stepts for you. Do not play with someone emotions, the world has another pace for girls like me. I am fast in every thing, almost everything. Being slow means rejection. If you reject, be brave to admit at least.
Messy comment but i think you got my frustration ;)
David on July 06, 2019:
As with everything in life, shyness and anxiety are on a spectrum. I see my shyness as if it were on a dial. The more comfortable I am with a woman, the more I trust her, the more friendly she is and the better rapport we build, the less shy I am going to be. If a woman intimidates me by being unfriendly, overly judgmental, gossipy, or cliquish, then I will act very reserved and shy around her. Each time a woman makes her interest known, whether through flirting, or progressing the engagement, or being receptive of me, the less shy I become.
Women like to feel safe with a man who she knows won't physically harm her or will stalk her like a creep. However, as a shy man, I like to feel safe with a woman who will make me feel accepted and understood. I get that many beautiful women will test for confidence, but if we have a good banter going then I tend to take those tests lightheartedly. On the other hand, if she comes off judgy or acts like higher status than me, then I will take them seriously. I believe that only makes sense, considering that we can tease and be sarcastic with our friends, but if we said the same things to someone who didn't trust us, they would probably take offense.
Unlike John, if a friendly woman who got along with me asked me out on a date, I would be flattered. I rarely if ever approach strange women. I am more of a "get to know you" type of guy and then escalate with humor and flirting over time. However, the more friendly a strange woman is with me during a situational conversation, like say at a bar or event, the more present I am with her and pick up on her signs and signals far more easily than if I had my blinders on due to her indifference.
The main thing that I worry about as a shy guy is how my shyness manifests itself in conversation. Often we guys are told that nervousness is a sign of being timid, weak, and awkward. So what happens is that I end up shutting down mentally in a sort of limbo between fight and flight. I am not some trembling leaf mind you, but I am highly neurotic unless a woman puts me at ease.
So ladies, just because a guy is shy and a bit reserved doesn't mean it will need a jackhammer to crack his shell. Sometimes it just takes a bit of friendliness and enthusiasm.
John on April 12, 2019:
Super shy guy here - do NOT ask me for a date or do any of these things suggested. My reaction will be to tell you I'm not interested in a relationship with anyone. Sorry, but you're going to have to wait for me to make the move. I have to do this by myself. And you shouldn't wait forever for me, because it might not ever happen. And I'm fine with that. I understand I may lose you because I didn't make a move, but oh well.
Ian Aka on May 21, 2018:
This is really good stuff. Its nice to see someone out there who understands shy guys.
Devika Primić from Dubrovnik, Croatia on June 17, 2013:
Helpful points here on dating shy guys, definitely these tips can help most individuals in such situations.
Derrick Bennett on June 16, 2013:
I use to be a shy guy I wish girls had done these things for me. These are great tips to boost his confidence.