Eight Flirting Tips to Bring a Shy Guy Out of His Shell

by Dr. Diana Kirschner on July 27, 2010

With a shy guy you have to be more available and flirty, take the lead more often and maybe even give him the first kiss.  Keep in mind, however, that he needs to be responding very positively to each of your moves. If he doesn’t, end the relationship because you don’t want to be stuck in a fantasy where you are crazy about someone who is truly not into you.  Now here are eight dating tips to bring a shy guy out of his shell:

1. See him when he is in his element.

If he plays sports, go watch.  Be there as he finishes a marathon. If he is giving a talk, try to arrange to be in the audience.  When a shy guy is in his element he will be at the height of his charisma and at a high point of self-confidence.  Bottom line: he will be feeling very good about himself.  And this means he will feel empowered to make a move on you if he is really interested.

2. Compliment him.

Notice something about him or what he is doing that you really like and praise it with a specific and sincere compliment. For example, That blog you wrote about going to Sicily was hysterically funny and made me want to go! This builds his self-esteem and will tend to get him to talk more about the topic.  And it may even get him to show off a bit for you.

3. Say his name a lot; give him a complimentary nickname.

This indicates that you are noticing him and that he is important to you.  He will bond more quickly with you when you use his name.  Also, choose a complimentary nickname based on one of his qualities that you admire.  For example, if he is into cycling, call him “Lance A.” This will get him to laugh and open up with you about his cycling experiences.

4. Ask open-ended questions.

Good examples are, “How did you get interested in (your job)?” “What brought you to live in the city?”  “How do you manage to train for a triathlon when you work full-time?” These kinds of questions will help a shy guy open up and talk about himself.  And this will lead to him feeling known and being comfortable with you.

5. Ask for help with something.

Men love to help women.  They are biologically wired that way!  Ask him to fix your computer, your car, your bike, your door—you name it.  He will enjoy coming through for you and feel much more connected to you.  Ask him questions about what he is doing—this will get him talking more. When he is in the “helper” role he is much more likely to share with you.

6. Ask what he likes to eat or what sports, hobbies, or movies he likes.  Once you find something in common, ask him if he’d like to do it some time.

Shy guys can be very interested in you, but petrified to make the first move.  It is very easy to open the door to a common interest by asking about food, hobbies or other fun activities.  When you hit on something you both love, you will instantly become more bonded.  It is easy, then to make the first move and ask about doing the activity together.  This is a good litmus test that will show if he is interested or not.  When you are opening the door that much, if he does not respond and make the date, chances are he is not into you.

7. When leaving, say you’d like to see him again.

This is an easy, non-threatening way to show that you are interested in him.  If he responds positively, by smiling, nodding or saying “yes” he may be feeling some attraction to you.  At that point, make sure he has your contact information!

8. Give Him a Mini-Massage

If you’ve spent some time together, make physical contact with him. Being physical releases oxytocin, the bonding hormone so he may feel closer and start responding to you immediately.  A mini-massage also relaxes him so that he is less up-tight and fearful.  In addition, making physical contact often opens the door to him making an affectionate gesture towards you later on—where he holds your hand, puts his arm around you or kisses you.

So practice some or all of these flirting tips and you’ll be an expert at bringing out the best in guys. And to help you I want you take advantage of my free ongoing support: You can learn EXACTLY how to find,attract and date great guys, find the One, deepen commitment and much much more by subscribing to my Dating Tips & Relationship Advice Newsletter, absolutely FREE!  Click Here to get started now.

Wishing you love

Dr. Diana

Diana Kirschner, Ph.D. is a frequent guest psychologist on The Today Show & best-selling author of “Love in 90 Days” (dating advice book)” out now in paperback (at Amazon) with a new chapter on “Dating Games Men Play.” Love in 90 Days was the basis of her PBS Special on love. Connect with Dr. Diana through her FREE relationship & dating advice newsletter.

{ 41 comments… read them below or add one }

Dr. Diana Kirschner July 21, 2011 at 10:08 am

Give it a try!!! Start with baby steps! Wishing you love!

ayesha July 20, 2011 at 8:43 am

i dont think so that it will work

XviD October 31, 2010 at 9:45 am

GUY HERE.

If you are halfway decent looking, or have big boobs, or nice clothes, or are IN to a guy , you WILL get him if you try at ALL. He might not ask you, because men are conditioned to NOT hit on girls because of feminist bullshit and sexual harassment laws and rules in the workplace.

GO FOR THE GUY, YOU WILL GET HIM 95% OF THE TIME
5% he is gay, he is afraid of his FD or doesnt want to get caught or doesnt want to cheat, theres something REALLY wrong with you, or he thinks its good to be true.

Mark October 28, 2010 at 9:50 am

Ei. I’m a shy guy. Any tips on how to find girls that will surely flirt with me? LOL.

http://theburnxtremereview.weebly.com/

Shannon October 27, 2010 at 12:54 pm

What about shy girls? It seems like many men don’t find introverted chicks attractive.

Shannon October 27, 2010 at 5:32 am

How about tips for shy girls trying to break through to men?

Dr. Diana Kirschner October 24, 2010 at 12:43 pm

Being warm and friendly is not a first move. Most guys need at least some encouragement to approach a woman.

juliana October 24, 2010 at 12:14 pm

If a man does not want you does not mean he will not use you. And do not believe women should make the first move nor call men.

Pete Pallein October 24, 2010 at 7:54 am

Very Good! Where were you 40 years ago? You sound like the ideal woman. Those are the greatest things any girl could do to make me resist. Looks and brains are nice, but sensitivity triumphs over all including sex.

shyguy October 23, 2010 at 9:14 pm

this is great, but overdone.
honestly, all you need to get a shy guy out of his shell is: say “hello”

yes I know it sounds like a bad joke but it’s true.

now come on, this isn’t useful information, give us the real useful stuff…

tell us SHY guys how the @%#@$@$# to get out of our shells and gather the nerve to ask that girl/woman out, seriously it’s horrible

what’s the worst that can happen if we get it wrong? well, there’s this picture in my head of me wearing a striped shirt getting free room and board in a very uncomfortable place…

candlelightfortwo October 21, 2010 at 11:07 am

Just wanted to say to all the shy guys…

Don’t let fear of rejection or heartbreak keep you alone. We all have those fears, except maybe the hopeless narcissist.
Keep the porn to a minimum. Fantasy has it’s place, but should never take the place of real human interaction.
And for the guy who fell in love and had his heart broken: Disappointment and setbacks are a part of life in all areas. The positive side to it is you ventured into a relationship. Now just don’t give up or set that as a precedent for any future relationships because that’s not the case. Obviously it just wasn’t the right match for you, but that’s okay. I choose to think of everything that doesn’t turn out the way I hoped as a learning experience in life rather than a catastrophe.
Anyway, please don’t make your shell impenetrable. And maybe learn about body language so you aren’t second guessing every nuance of interaction with a woman.
Okay, I’ve put in more than my two cents. Loved the article, will buy the book.
PS I’m a woman in case you were wondering…

Dr. Diana Kirschner October 20, 2010 at 12:35 pm

Yes it does. But…..

Dr. Diana Kirschner October 20, 2010 at 12:32 pm

The great zen monk Joshu was asked “what is the nature of enlightenment?” He said simply “Attention.” The students wouldn’t give up so they asked again. Joshu said: “Attention, Attention. This went on for awhile until finally he said, Attention, Attention Attention.
Wishing you love
Dr. D

goldendemon October 20, 2010 at 11:23 am

was married for 38 years she past away last year butwe did most things together aim a avid fishermant she did not like it as much as i did but did go with me lot of times that made my marriage
work god bless her,

anne - marie October 19, 2010 at 11:41 am

I am not fond of making the first move being a female.Yes i think shy people should be more than loved. I think they should be cherrished, and held, cuddled and supported. I was once shy,so was my husband. It was a sad and lonely time. I did something similar , except it was all part of a fantasy i had about him and I. I was given advice and never used it.Now I have been with my older husband for 17 yrs. And the life of these 2 shy people have flourished and still do.

As for the other shy people out there in this world. Do not put your heart on your sleeve. Just don’t box it in too tight that it can not be released. When your true companion is ready to show , you will know what to do. I wish all nothing but complete happiness and bliss. Life is what you make it . Good luck ,
Anne-Marie

some guy October 17, 2010 at 11:14 pm

i’m a shy-ish guy…
and that would definitely work on me…

so if you see someone who is wearing jeans, a sweatshirt, (which do not match) and, uhh, 6’2″
black hair… green eyes… nevermind.
it would work.

jesse October 16, 2010 at 10:59 am

i am very shy. i never realize when im being hit on. i never get the subtle moves cause all my brain is thinking is what do i do next. is she really into me. did she just try a move on me, no couldn’t have been one, she accidentally brushed u against me and i dont realize till days weeks months later when i think bck that she was droppin some pretty big hints..its funny and embarrising to me because i now i am very good looking ( as people have told me my entire life) but i still do not have the backbone t be with a girl..ftw

jessi October 15, 2010 at 3:17 pm

Showing up at his door naked with a six pack works every time too.

A classic shy one October 15, 2010 at 4:39 am

Good tips but don’t forget shy guys may like a little assertiveness. A nice coy smile at just him, the classic wink, and when you leave a quick friendly kiss on the cheek can be that shock to get him to turn your way!
Oh and get used to it, he’ll always be shy and want you to take the lead at times. But the rewards and romance us shy guys offer are the best!

super October 14, 2010 at 4:53 pm

Spot on for me, but the thing is, i actually am more of a supporter, and love to help out. Its just in my nature to help someone or something in need, perhaps my greatest downfall or my greatest strength

DPU....... October 14, 2010 at 12:00 pm

I think these tips applicable for both(men and women)

meh October 12, 2010 at 6:39 pm

I don’t agree with “Keep in mind, however, that he needs to be responding very positively to each of your moves. If he doesn’t, end the relationship because you don’t want to be stuck in a fantasy where you are crazy about someone who is truly not into you.”
If a guy isn’t responding positively, you are probably going too fast for him. That’s how my (short) relationship ended. She was basically my first for a bunch of things (kiss, makeout, girlfriend, date, etc.), so I was not accustomed to her advances. We went from making out on the grass to her straddling me above (towards stomach) my crotch. I felt nervous as hell, so I didn’t really respond “positively”. I started to feel better and ready, but then she told me it wouldn’t work out.
If a guy doesn’t want you, he’ll tell you.

spisteel October 12, 2010 at 6:38 pm

Well, it’s midnight here. Am laying down on my bed and reading this Post. Was reading some advanced hacking Doc. I clicked some links here and there and at the end of the I landed in this site. Well, this is something cool. But, am now feeling very much alone after reading this. I don’t know in the road or in the office how many girls have starred at me, but I had just overlooked them, considering them just as passer by……….. Suddenly, I am feeling bad thinking about them…….. :(

nyway, time to sleep. Time to dream. I have to go to office early…….steel…cya.

Burn Xtreme October 12, 2010 at 4:38 am

I confess; I used to be a shy guy What is a shy guy? Any guy who fails, refuses or can’t bring himself to approach women. These guys usually won’t say one word to a girl unless she speaks to them first. Everyday they pass by available women who flirt with them and would love to talk with them but these guys do what I used to do; clam up turn tail and run for the hills. Speaking from experience, this fixable disorder forces guys to use their shyness as an excuse for not engaging in healthy relationships with the opposite sex.
http://burnxtreme.org/

Dan Geraghty October 8, 2010 at 7:29 pm

I’m a very shy guy, never really having the courage to even talk to a girl let alone make a move. I can say that the advice you’ve given is pretty sound in theory. If a girl followed your advice to attract me I’d say it’d work brilliantly. Some guys are more shy then others and, no offense to any guys who read this, and be pretty dense. Alot won’t realise that the girl is interested and mistake it for friendship only and if a shy guy thinks that a girl just wants to be his friend then he’ll be as good a friend as he can be but he won’t make a move.

John October 7, 2010 at 6:07 am

Brad, that’s just the nature of some girls and hardly Dianas fault. It sucks, but it’s part of life that some run away from love. But wasn’t the attention better than the alternative of never getting anywhere, as we shy guys usually have it?

Person 023, -oh yes We do! I.e. talking or performing for an audience is hardly the same as making it with a girl you fancy. Nor is being good at sports. Or being highly intellegent. Sometimes these things just makes it worse because no one thinks it could be like that. With some you wouldn’t think it, but it’s just a matter of how perceptive you are. Lots of people who’re shy when it comes to getting past first base are social and outgoing and seem not to have these kinds of problems.
A good clue is someone that seems like a great guy but you rarely or never see them having a girlfriend, date or even the occasional snog even though they’re obviously attracted to women.

Great that someone takes the time and effort to tell women how to reach shy guys. As a secretly shy and sensitive guy that’s usually being percieved as “just being picky” or “choosing to be alone” (as if anyone really would), I really appreciate it.

Foreveralone:( October 5, 2010 at 4:51 pm

Just gotta say that people are different, I dont like that girl says my name or that she compliments me… Best tip is to be his friend, no one is shy with his/her friends. When you are at friend level, you get to know him better. Knowing other person is allways a good thing. Worst scene is that when you both are shy… You cant know the real “feelings”. I am shy when I have not drink alcohol, when I boost my ego with alcohol I became my alterego or something like that… When I drink I get contact with girls. Only downside is that no one takes that drunkshit seriously… And when I am clearminded again I cant do a shit… My problem is that I am affraid of fail so bad that I cant do my move. And when its case of another shy person, you wait and she/he wont do the move you became paranoid… Now I am in this situation… I dont know her feelings(Ive heard that she likes me but… I am just not sure) I have feelings towards that girl but I just cant do a shit.

seraph5555 October 1, 2010 at 3:54 pm

as a shy guy i gotta say this is pretty spot on

shures October 1, 2010 at 7:00 am

tips for guys

shures October 1, 2010 at 6:59 am

nice

Andrew October 1, 2010 at 5:34 am

All good advice, Dr. D, but you under-estimate the degree of shyness and fear of embarrassment many men feel. If a woman did these things toward me and followed your advice she would give up on me and never know that about a year later I would suddenly realise that she might have been giving me the green light to make a move. Too late by then!

Dr. Diana Kirschner September 30, 2010 at 5:37 pm

I’m very sorry that happened to you. But there are plenty of great women out there for you. One may actually read this reply and want to contact you.
Wishing you love Dr. Diana

D September 30, 2010 at 5:06 pm

That’s not necessarily true, Person023, I would probably consider myself shy, yet I have played competitive sports all of my life, and I love taking the lead in group activities. My one problem seems to be in actually meeting girls, and starting the conversation, once we’re talking, I have no trouble at all.

DesiColours September 30, 2010 at 4:03 pm

@VB

LOL, there are other solutions for shy women :P

Aladin September 30, 2010 at 2:58 pm

@Person023

You are wrong.
In my culture it is a good quality 2 be humble..in western culture it is called shy… I would not call it that.
But even though I am humble in conversation.
I played competitive in sports, even got in selection team.
And about pblic speaking.. i gove workshops…
so I proofed you wrong.

Brad September 30, 2010 at 9:03 am

A woman recently used ALL these techniques to seduce me, only to break my heart as soon as it got serious.

Thanks a funking lot!!!! I fell in love with her!

Person023 September 30, 2010 at 5:45 am

If a guy is shy he won’t be giving a speech or usually playing competitive team sports.

satish jindal September 30, 2010 at 4:21 am

tips for performing sexual action does not require any guidelines.it comes automatically or not even you try hard for it.

RP September 29, 2010 at 4:19 pm

No one has ever flirted with me…I feel better after reading this..I can rest in knowing I didnt miss anything

Dr. Diana Kirschner September 27, 2010 at 12:16 pm

Absolutely.

VB September 25, 2010 at 2:29 pm

Can a guy use the above tips to flirt with Shy Women ?

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