How to Crack The Shy Guy
May 2, 2009 Posted in Advice, Relationships

Ah, the Shy Guy: that rare specimen of man who you’ll never overhear talking bragging about some meaningless hook-up. You won’t find him at parties or see him hamming it up for the ladies. He’s sweet, modest and avoids being the center of attention at ALL costs. Odds are, he’ll be the one sitting in the back of class, avoiding eye contact with the professor when he or she scans the room for a volunteer.
He’s pretty much adorable, really. Mysterious, intriguing, sensitive, endearing … a diamond in the rough (“the rough” being the obnoxious, masochistic guys that are just way too common in college). Shy guys are hot. Think Michael Cera. Mmmm.
No? Just me?
Anyhoodle. You’ve caught him glancing furtively in your direction on many (many) occasions. You’re interested. He’s interested. But the two of you both know there aren’t gonna be any suave, hey-baby-what’s-your-sign moves on his part. So, short of holding up a “Hey. You’re cute. I’d say yes if you asked me out” sign, how d’ya go about meeting/cracking open the shy guy?
Approach him casually and strike up a small convo. While he prrrobably won’t be bowling you over with witty banter and charm, he won’t run away. Do most of the talking, but toss in lots of open-ended questions. Just keep it light and impersonal at first: topics like homework, professors, something on the news. Do this a few times a week to establish a bond and tear down that wall he’s got up.
Spend time as friends, without pressuring him about dating. Hang out with him alone, rather than with your other friends. Be patient. It takes the shy guy some time to become relaxed and show his true self.
Be approachably attractive. The root of shyness is insecurity, so it’s more than likely that he thinks you’re out of his league. So now isn’t the time to try out cutting edge fashion or over-the-top makeup. Try for “cute” rather than intimidatingly gorgeous (that’s a toughie, I know).
Arrange a few quiet dates if he doesn’t get up the nerve to ask you out. Keep it casual, and— again — keep it one-on-one. Clearly, the shy-guy isn’t going to do well in a large group of your girlfriends shrieking about vibrators. Choose something low key and easy like a movie, where there’s less pressure to talk.
Gauge his feelings for you. Talk about what you’re both looking for in a person, and drop hints that what you’re looking for is him.
Help him feel confident around you. Every male has an ego — find ways to boost it sincerely. Subtly compliment him. Let him help you with something, whether it’s a homework problem, fixing your computer, or finding the latest gadget. Or — and this is probably the best confidence booster– see him when he’s in his element. He’ll be MUCH more open and charismatic when he’s somewhere he feels totally comfortable.
Once you enter the relationship zone: First of all, yay. Second of all, introduce him to your friends and family slooowly, starting with the quiet, less intimidating ones. Yeah, save loud Uncle Frank and Over-The-Top Tina for when he’s more comfortable in the relationship.
The shy guy is SO worth the effort and patience. Think of him as … a gift. A treasure to unwrap. A rare and special treat that not everyone gets to see. If you can stick out a few awkward silences in the beginning, I guarantee you’ll have landed yourself a respectful, fun and totally caring guy.
[Photo courtesy of MariaTarescaCB on Flickr.]
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Jess says:
Sat, 2nd May 20091:28 pm
haha aw.. I'm def the shy girl and these make sense to me too. Catch me in my favorite class and I'm a lot more outgoing than any other place.
shy boys are nice, but shy girl + shy boy doesn't really go anywhere.
Sarah says:
Sat, 2nd May 20094:03 pm
I'm an extremely shy girl and while this is a great article, it's a teeny bit patronising to shy guys. You make it sound like they can't do ANYTHING social by themselves and you're going to be doing ALL the work in the conversation. Unless they're completely social phobic (I have mild social anxiety disorder myself so I know what I'm talking about), they probably quite able to maintain a conversation. Generally good tips though.
michelle says:
Sat, 2nd May 20095:59 pm
hahaha, o god, i was trying to date a shy guy and I did exactly the OPPOSITE of everything on this page… I invited him out to dance clubs in the city, I talked about vibrators… I got all enthusiastic about meeting my family (my loud sister and mother) and now we are not really talking to each other..
any chance I can redeem myself?
Amy says:
Sat, 2nd May 20096:43 pm
I know two very shy people who have been together for years–on their first date, they didn't even talk, just sat around staring at each other. I have no idea how they even knew they liked each other!
Grace says:
Sat, 2nd May 20097:31 pm
ZOMFG this came like a month too late
Sam says:
Sat, 2nd May 20097:42 pm
"shrieking about vibrators" LOL
A shy guy says:
Sat, 2nd May 20098:03 pm
Ha…I just stumbled across this article via google (googling about the Swine Flu, of course, lol). I feel like this article could be talking about me, because I'm a very shy type of guy.
One thing I noticed is that a lot of women are ill-prepared to interact with us shy guys.
If it matters at all (to all the ladies), from a shy guy's perspective, this article hits the nail on the head.
You know whats insanely weird, though?
As I was entering this comment I noticed this article was authored by someone from VCU…and I go to VCU.
Cool article, though.
Meg says:
Sat, 2nd May 20098:15 pm
I agree completely! I have been dating the shy guy for 2yrs and 3 months now, and I wen through all of these steps to get to know and date him. It was worth every minute! He is the most amazing guy ever. =)
Samantha says:
Sun, 3rd May 200912:46 pm
Good advice! I always wonder whether the boys at my school think too much of themselves to ask the girls out, or if they're just shy and afraid of rejection. It'll be good to keep this article in mind for when I find one I think is the good kind.
Also, are you using "masochistic" the way you want to in this article?
Sarah- Virginia Comm says:
Sun, 3rd May 20093:19 pm
@ Sarah: Aw, totally didn't mean for it to come off as patronizing. I am actually an extremely shy person myself … a lot of this "advice" came from my personal experience in things that make ME feel more at ease when meeting new people.
@Samantha: I … uhh … no. I'm not. Haha. Minor-ish typographical error on my part. OOPS.
Karina says:
Sun, 3rd May 20094:02 pm
Great article!! Im pretty shy myself sooo talking to that shy guy can be a little tough. And I go to VCU as well haha. Keep writing, I would love to hear more from a fellow Ram!
Joe the Drunk says:
Sun, 3rd May 20095:32 pm
after you crack the shy guy, how do you get him to crack open your ass? do you then ask him (politely, without hurting his feelings) to stick it in?
Kim says:
Sun, 3rd May 20097:38 pm
I thought your article made some great points. Maybe the shy guy is just waiting for the right girl.
BTW, Joe the Drunk must really be in-touch with his feminine side to be so up on the latest on the College Candy website.
Liz says:
Mon, 4th May 20099:45 pm
I am dating a shy guy right now. We have been only together a week. He is really prude I can't barly get him to hold my hand let alone gig me? What do I do? Any tips. I am not used to going this slow. He is still a complete virgin. He hasn't kissed a girl and will be 21 in November?.
Liz says:
Mon, 4th May 200910:08 pm
am dating a shy guy right now. We have been only together a week. He is really prude I can't barely get him to hold my hand let alone hug me? What do I do? Any tips. I am not used to going this slow. He is still a complete virgin. He hasn't kissed a girl and will be 21 in November?.
Bethany says:
Tue, 5th May 20097:03 am
Great timing CC. This is exactly my life right now. Only instead of one on one it's me, him and his best girl friend.
Saul W9 says:
Tue, 5th May 20094:06 pm
As a shy guy I can say that if I was even remotely into the girl using these strategies, they would totally work on me. And not all shy guys are prudes – especially in private.
Liz says:
Wed, 6th May 20095:38 am
Thanks for the advice. But I think I have found the pride one. Unfortunately. I don't know how I am going to get used to it. This very different than what I am used to. Not to say I slawya take things fast but this is just really slow.
E says:
Fri, 8th May 20096:49 pm
Liz, what I'd say to you is just to be patient, but that doesn't mean you can't playfully prod him along a bit if he doesn't get incredibly awkward about it. Also since he's a virgin he might be a little(or a lot) worried he doesn't have the skill or know-how to please you. I guess the main thing I'm trying to say is you can't really rush people, it takes time to become comfortable with someone. I suppose I'd be classified as a shy guy, and I can relate a story about one of my high school relationships. This girl I was dating was very bold, had been with a lot of men, and she was my 2nd sexual partner (my cousin set us up together). She had kind of pressured me into going all the way with her, not that I didn't enjoy it, but I still had a hard time opening up to her. Well, she broke up with me a month and a half into the relationship saying, "Your cousin told me it'd only take about a month for you to really start opening up to me, and it's been a month and a half already." Of course I thought, "How dare they?! They just decided I'd open up within a given time, and for not meeting this criteria I had not even known about, it's suddenly over?" I was hurt, and naturally I was angry at both of them, her for rushing me then suddenly dropping me and my cousin for deciding things in MY relationship that they had no right to. My next girlfriend and I took things slowly. We just talked and hung out for a few months before anything sexual happened (but when it did, boy, did it ever!) and it really gave me the time I needed to feel a real closeness to her and got me comfortable with talking about pretty much anything with her. In summary, if it's a relationship you really want to pursue, try to be patient and be sure to openly tell him how you feel, and encourage him to do likewise. Good luck!
Liz says:
Sat, 9th May 200912:10 am
E, thanks a lot for the advice. I really do want to pursue it. I waited almost a year in half to date him. I liked him but didn't tell him. Becuse I thought he would never like me. He's not very touchy feely. As much as I get teased NY my friends I will just have to wait. I told him I will take things at his pace. This is also long distance. We met at college. We live about an hour away. He told me that he fell in love with me. Is he really meaning he fell in love with me or is that his way of saying he fell for me? Thanks for all the great help.
Ryan says:
Sat, 9th May 20094:36 pm
I completly agree with everything in on this page (for the most part) there can be so many reasons why we are the way we are but its better to take it slow rather than pressure us to the point where we cant be ourselvs.
I've never been good with expressing myself anround many people if i dont know them, once tho I found someone who after getting to know ment the world to me but pressured me to the point where i couldnt be myself and then left me for it…been so long since then but now im too afraid of the same thing happening to even think about trying again…now i keep myself out of the way so that when the day is done i can dround out my thoughts and feelings in music.
Im nice to everyone so I dont have to worry about upsetting people but after her I just got to the point that i try to repress fellings and build my wall pretty high so i cant be hurt again…
take my advice the pressure dosent help…
someone says:
Mon, 18th Jan 20104:21 pm
Great article!
But I have a follow up question
What if he acts nonchalant and just really relaxed/cool….is she shy or just doesn't care?
Because there is a guy in my college who I noticed look at me quite a bit…but he also looks around at everything/everyone else.. and i dont really look too closely to see a difference cause I'm shy as well.
We used to have a class together and now we just take the same train home together and i see him around campus sometimes…
I really dont know how to read him… it's impossible. he seems so composed/bored/relaxed all the time. even the way he walks is cool.
Chelsea says:
Wed, 20th Jan 201011:03 pm
This article is awesome, but a little too late for me.
I need some opinions here. So, I've been seeing a shy guy. I did a few things right, such as indulging his ego, taking the lead, making the first move ect. But, his shyness and insecurity started to make me feel insecure because I didn't know if he was interested and I started to over think the fact that I have to do all the work. I didn't know if we were dating and I also started to feel like he was still looking for other girls and that he possibly was only settling for me because I'm less intimidating than the super pretty, tall, skinny girls. So, I did the WORST thing possible; I kissed another guy. He later caught wind of it and asked me up front if I kissed someone else and I was honest and I said yes. I explained that I was confused and that I didn't think he was interested.
He then explained to me that he is simply shy. He accepted my apology, but he rarely talks to me now. So, I've basically lost his trust, wounded his self esteem, outed his shyness and insecurity(which I hear is the worst thing you can do to a shy guy) and made him think I'm the bad guy. Is there any possible way to fix this? I really care about him.
Loser says:
Tue, 1st Feb 20114:23 pm
well being shy guy myself, i was never being able to get involved in any relationship with a girl. from the age of 15 to 25 i was oretty cool being alone, but after that age a become desperate and needy, experienced quite a few rejections that makes me inferior to women, after the age of 30 i have made the decision to give up after one bad rejection. She rejected me badly in pubklic after that i started use strong depressants that lower my libido very rapidly, now i am feelinh sorry for myself for having no sex in this life..I am still crying from time to tome, but i know i will never be able to make another move.
I am alredy cluless ass, scare of women to death, i even do not know what i would do with some…
The weed however makes you feel good with your loser-like life style…
i have no advice for you shy guys, there is no happy end to my story. I tried everthing and nothing worked.
JaC says:
Wed, 23rd Mar 20118:23 pm
Hola sweetie, don't give up..you're not a loser. There is nothing wrong with being shy and we have all experienced our share of rejection. So you haven't had sex yet, who cares. It's not the end of the world and in fact being a virgin is a rare and special thing (I am still one at 28) You know how many people are jealous of that and wish they still were? that's the way God intended it to be.. you get married then you get to experience sex with that special person. I guess I'm trying to say just have confidence in yourself. People are naturally drawn to that and find that attractive..
When the time comes and you meet that special someone, you'll be willing to open your heart again and so will they. In the meantime: let's enjoy the single life and being able to spend however much amount of time we want doing our own thing!! I pray that you do know/or will get to know God and get to experience his love as well. He loves us regardless John 3:16 "For God so loved the world that He gave his only begotten Son, that whosoever believeth in him should not perish, but have everlasting life.
Nikki says:
Wed, 30th Mar 20118:24 pm
You are not a loser. Have faith.
Leah says:
Sat, 16th Apr 20118:52 pm
I have fallen for a guy who I think is shy. He is absolutely adorable! Being shy is nothing to feel bad about.
I just hope he’s shy rather than uninterested. He kissed me when he had been drinking at a party, and put his arm around me and told me it was great to finally hang out with me. But after that-nothing, until the next party.
Wish he’d ask me out!
Angie says:
Sun, 24th Apr 20111:34 pm
Hey! I dont even know you but I must write!
You have not tried EVERYTHING so clearly your story is not over yet!
I ran across this article while researching because of a shy man that I liked so much but felt rejected due to his being too aloof. He was gorgeous with perfect body so I had a hard time believing that he just wasnt expierenced with certain sexual activities, as he was telling me. I thought he was lying. I know that having a shy, introverted, or even just quiet personality isnt the most praised in our culture, therefore it becomes misunderstood. Im a total sucker for the quiet, shy type and always have been, but its rare to meet this kind of man. Even my best girlfriend is very shy until she gets to know someone. I adore this personality because once this person opens up, its truly like a gift that lets me know that Im special because so few people get to see this side of the individual.
Angie says:
Sun, 24th Apr 20111:34 pm
Also…
But I can say what you are craving is not going to be found sitting at home smoking weed.
Its only a temporary comfort isnt it?
I am so very very sorry to hear of this event that took place for you in public. I do not know the details but rest assured that a real women, would never do that to anyone for any reason. She clearly had her own inserurties to make her behave in that way in public. I have a feeling that if you are out interacting enough socially, and making your presence know, your girl is going to find you and just like in the case for me, maybe she will have a strong enough personality that will not need a foward male!
Former Shy Guy says:
Sun, 10th Jul 20116:25 pm
I have scrambled across here through an internet search and would like to add my two-cents. I am 26, male, and can relate to many of the comments on this blog.
By no means am I immune to moments of shyness. I also recognize a great deal of personal growth lies ahead in my life. That said, I now consider myself to be more of an introvert than shy person. I do believe there is a significant difference.
I think for the women posting here, it is important to understand that a man has to feel comfortable in his skin, period. I am not quite there myself but do feel improvement every day.
A few experiences and facts about myself:
-I was a virgin until age 21, ( and closer to 22, at that)
-I am a musician and was playing piano on cruise ships at age 20 (imagine that- prime real-estate for hooking-up and gaining experience) yet was so shy, I never kissed a single girl the entire 4 months.
-I have always been, at least until my mid-twenties, unconsciously seeking approval and giving my personal power away to others.
In hindsight, I now see how my shyness was rooted in insecurities. When I look back to my teens and early 20's, the experiences I could have had are numerous. I want to have children one day and will definitely teach my son what I have learned.
Where I stand now:
I am focusing on improving my career & education. This feeling is empowering and in itself gives me great confidence. I am also 100% comfortable talking to anyone, in any situation.
While I used to place a high value on friends, social life, and finding a 'girlfriend', I have made a 180 turn in the way I look at life. My focus is now more self-centered. I realize women and social life will be consequence of my career and personal growth progress.
What has improved my confidence greatly is recognizing the power of my mind. If I am ever in a situation where I feel I am losing mental control, I find great power in transferring my though process to a situation of success. For example, I have composed music of which I am very proud of (which I also expect to earn alot of money one day too!!) Now consider which is more difficult, this, or talking to a woman (or anyone, for that matter) ? You see? It is all in the mind. When you think about it, insecurities are so ridiculous, it is silly.
My advice to Guys:
Focus on making money, improving your career, health, fitness, and being a good person in general. Focus on improving your mindset. Treat women respectfully, but make sure you enter relationships on your terms. Also, make sure you have your own personal fun (flings, hookups, etc, if this is what you are comfortable with) too, and yes, their is a way of doing this being fully communicative and respectfully. Always put yourself first while maintaining your integrity.
My advice to girls: If you like shy guys, yes, it does raise our confidence when you talk to us. We appreciate that. Having said this, don't expect to much from someone who isn't comfortable in his skin. I am being honest here. Learn to recognize the difference between shyness (in my opinion it is a mental health issue) and an introvert. (a much healthier and desirable quality) An introvert may not have many friends, may be quiet, but is still able to talk to you and anyone he feels necessary. That is not shy.
lol says:
Sat, 30th Jul 20116:15 pm
Joe^ trolololololollololol lmao!
Marc says:
Sun, 4th Sep 20115:59 am
Im a shy guy myself, Im 20 never been on a date and never kissed a girl. I really liked this girl that I could .ever go up and say “Hey” Then one day she came up to me and of course I was set back and very nervous. She talked to me a little more each day which in turn made my comfort level with her grow and after several weeks I was comfortable enough with her to sit there and have a convo with her. But then I seen her with her friends and looked at her smiled and waved hello, Her friends laughed and she said “Who are you” And they all had a good laugh at me. I seen her chatting up some guy later and of course my heart sank. Since then i’ve become terribly shy towards girls and my confidence towards girls is equilly bad.
. says:
Sun, 11th Sep 20112:39 pm
I just wanted to say that I’m a shy girl and would agree that this is the way to go when approaching most shy people (obviously depending on the degree of the persons shyness/introvertedness as we are each very different people with a similar quality.)
I’m about to be 21, and I can honestly say that I’ve never really been in an official relationship. I’ve done some flirting with guys I’m comfortable with, and have admitted feelings for a few throughout my life so far but never have I had an actual long term boyfriend.
When I was around 15 or so, I didn’t really feel too comfortable admitting this, and I agreed to go out with this guy that I actually did like, but I never got his number or gave mine out to set anything up. This was before a Christmas break in school and when we came back we didn’t even talk and he started dating this other girl. I wasn’t hurt very much at all because I felt I deserved it and really, I did. I felt aweful, but I do remember that he did pressure me into giving him a straight answer and I was way too shy to do so even with knowing that he liked me already. We stayed friends although it was a tad awkward for a bit after.
I never have a problem with guys hitting or flirting with me, I just seem to have a problem with saying what I want to them. Unless it’s a weird obnoxious guy, then I tell them straight up to leave me the heck alone! haha
I’m still doing a lot of figuring out on my part so I’m happy being single. I now know that nothing will happen unless I’m ready. Even though on countless of times I feel as though I am ready and depending on the situation, make an awkward fool of myself haha.
However, there is this one guy that I really do quite like and he is also a bit shy himself. He’s an old friend of mine. We used to be best friends but I moved a few times since our old friendship. I remember liking him then but I wasn’t as accepting of it seeing as we were friends and all. He is in the same boat as me, no relationships, and that’s as much as I know pertaining to his lovelife.
I realize our situations and even though I like him, a lot, I’m still not ready and I’m not sure if he is ready as well.
I’ll be ready when I’m ready and he’ll be ready when he is ready (if he is less or closer to it than I am).
If I reach it first, I might possibly wait for him and it would probably be easier for me to do so considering I know what it’s like from experience.
So, to end this gigantic, rambling mess I’ve written, I’ll leave with hoping you all figure yourselves out before you try going into anything that is forced on you!
Yes, this also means you less shy/introverted people because no matter how you are socially, anything forced is most likely not going to last. Relationships need a solid base to be built on and that takes time.
Each of ourselves also need to be solid because we are the pilar holding the relationship, if it’s not solid it will eventually collapse. Both of them, one, or the whole thing depending on each of our situations. So look at yourself in the mirror and reflect. May sound stupid but trust me, it helps you gain insight on yourself.
PS: That last part also has a lot to do with what you’re looking for. Solid relationship with someone, or just flinging yourself around.
Either way, just be yourself.
Barry says:
Thu, 12th Jan 20124:14 am
I LOVe your reply and have a question! I also used tobe shy but transformed into a guy who could meet and date women really easily (after a ton of work to improve myself). I wrote an eBook to help other 'shy guys' too, but find that most guys don;t call themselves "Shy".
What do you think is the best way to reach guys like we used to be? If they saw a book called "How ____ Guys Can Meet Women" Or "A _____'s Guide To Meeting Women" what would most guys who needed help need to see in that blank to say "Hey that's me!!!" ?