So I like this guy, but he's uber shy and doesn't pick up on my subtle flirting. What's something I can say to bring him out of his shell to flirt?

“A little flirt never hurt ya know.”

“Hi, how are you?” didn’t work?

Maybe the fellow is going to tell his grandkids about the girl he’s sorry he missed in 2010.

Look, just tell him that you met this guy and you really like him. As your friend, you want his advice. So ask him, “What’s something I can say to bring him out of his shell to flirt?”

When he answers, say “Oh! That’s brilliant! Thank you!” Make sure you repeat what he said. Ask him to say it again because you don’t want to mess it up. Tell him you really like this guy and you don’t want to mess it up… so repeat it again if necessary.

Then allow a short 15–30 second uncomfortable silence to pass between you.

Then reach out and touch him and speak his name softly and sweetly. When he makes eye contact, Repeat what he answered right back to him.

what ever you do don’t do what RealEyesRealizeRealLies said to do!

Yeah don’t listen to me. I don’t know nan.

Are you two already friends, and you’re trying to slip into a more intimate relationship?
Or do you two see each other in class or something, but not really interact much?

What’s your age range?

As an uber shy guy myself, I find in the classroom settings I am extremely uncomfortable, and I lose my “bearings” so to speak. Any kind of subtlety is completely lost on me because I’m not in my environment.
If this is your situation, you might want to try to get in contact with him outside of the classroom setting. Or be more blatant about your interest in him.

If you’re in the “friends” situation already and want to get closer with him, what kind of social situations are these? do you hang out in big groups of like 15 people? Do you hang out with 5–6 friends? Are you two ever together, without other people?
Large groups are a bit intimidating to me, I always find myself retreating into my mental shell and mostly being an observer in the situations. On top of that, I tend to typically assume people are joking around. I joke around with plenty of my guy friends (to whom I am not attracted, just to be clear) with flirtation, because the awkward reactions you can get are funny.

If this is the situation, make sure you’re continuing your sign of interest as the group size dwindles down. Make sure he realizes you’re serious, and not just doing it because it’s funny.

All in all, try to make sure your intentions are more clear.

When I was in high school, it took about 6 months of flirting for me to realize that the girl was actually interested in me. It took me until one of the nights that everyone else had gone home and it was just us two hanging out. It took me until she continued the flirting with no observers around, to realize that she was actually interested.

To an uber shy guy, just you talking to him may be intense on his scale of interactions with females, so just talking to him may be plenty.

How about “You know, I think you’re pretty cool!”

Tell him you like him and invite him out for coffee. And maybe give him a kiss on the cheek before walking away.

He might be shy because he’s into you too, but doesn’t have the self esteem to follow through with it yet. By taking that off the table, you’ll give him the benefit of knowing where he stands in the situation and he’ll become more comfortable as a result.

@Fieryspoon good answer i like your style. shy guys fear rejection, or so i hear they do :)> this is sound advice. I thought I would share this for all the shy people out there…maybe it will make you worry less:

I am in my late 20’s, and I have never been in a relationship. Until recently, I had never even been on a date. And yes, I am a virgin. I have always been mildly shy my entire life. My shyness increases exponentially around attractive women, and I am lucky if I end up talking only halfway as an idiot around them. I am the guy who is likely to face plant into a closed door while trying to begin flirting with the cute casheir.
I am your average Joe physically. I asked a girl out on a date about as smoothly as a rampaging bull in a china shop. She was kind enough to accept. I spent the entire week before the date trying to educate myself on how to be a good date. I had no clue after all – it was the first date I had ever been on. Every day I would browse the internet for dating tips, ask friends for advice and try to think of things to talk about. I even asked my sister for fashion suggestions. By the time the date rolled around I had a million and a half things running through my head. “movie dates are bad first dates because you don’t talk….don’t bring flowers on a first date its a bit much….try to keep talking and avoid silence…. avoid asking her about dating history”
I am sure experienced dates laugh at these thoughts but to me everything was new. I went on my first date ever, acutely aware that the majority of women see shyness as a turn off. “It makes guys look immature” one of my female coworkers told me once. Now, I had initially prepared myself to meet her by sort of centering myself into a non shy mode that I seem to be able to reach once I know people for a long time. I would have been somewhat ok if she looked like she had online. Problem is that she was more in “WAY out of my league” category than I could have ever thought. You know the kind of woman that is attractive enough keep your attention enough to make you miss the chair you are trying to sit down on? maybe that’s just me. Ya I wasn’t ready for that. I was taken completely off guard and reverted into the stuttering fool once again for the entire night.
She was an awsome date in my opinion – intellegent, good natured and just an all around good person. She obviously was trying very hard to keep the conversation flowing. Yet because of my shyness and lack of confidence I just couldn’t keep the discussions going very long. Most of the date was spent with long silences as I frantically trying to think of something new to ask. I really liked her, I just wasn’t sure what to say to her.
By the end of the date I was utterly sure I had done terribly and felt as though I would never hear back from her again.

As I said before, I really liked her -so the next day I decided to at least give her a call. I got an answering machine and left a message inquiring if she would like to go out again sometime. I didn’t expect her to call back but figured it was worth a shot.
My phone rang a few hours later.
As it turns out, she wasn’t thinking about how I wasn’t keeping the conversation going. She wasn’t focusing on how odd or awkwardly I acted. She didn’t even notice most of the frantic questions that weren’t well thought out.
What she was thinking about was how she wasn’t keeping the conversation going. She was focusing on how odd and awkardly she acted. She only noticed the frantic questions that she had asked.
In fact, she didn’t think I was a bad date at all. She actually enjoyed herself and wanted to go out again.

While I was so busy worrying about her not thinking I was a good date it never occurred to me that she might be worried too.
We have another date planned now and this time I intend to concentrate less on how I feel and more on how she feels.

@germanmannn . That is one long story, good though. Normally people keep away from long ones, so try to keep it as short as possible.

It depends on how old he is.
If you guys are a bit younger, maybe try something cute, like passing notes or sitting next to him in class.
If you guys are a bit older, turn up the flirting (non sexually).
You have to remember with shy guys, that they may not be as experienced in picking up flirtation as a man who is experienced with women would.
You have to be more direct with the flirting, but don’t give it away so easily.

..or maybe, is he playing the chasing game and pulling you around, hmm

Just keep talking to him normally and when he gets comfortable he’ll come to you with that stuff, when he knows youre not going to slap him in the face or get mad. He just doesnt know that you want it, and he’ll get away with it unharmed. When he starts flirting its because he feels really safe around you, because he knows youre a positive person.

Stick a pair of panties into his coat pocket and mention to him the next day that you have lost yours.

Try a more direct or obvious approach. Let him know that he’s got your attention and you’re interested. Then, it’s his turn to make a move.

If he doesn’t – it’s quite possible that he plays for the other team if you know what I mean. Or he’s got someone else.

Not everyone responds to flirting. Some people like playing games, flirting, chasing and others are more straightforward. I personally don’t care for flirting myself or someone doing it to me. I see many girls/guys that flirt even when they are already with someone, and many do it to just be a tease. You need to be straightforward with him here, if you have a friend have them tell the guy you like him and you want him to ask you out or make small talk with him or ask him if he would like to join you for something or ask for his help with something, even if you make it up. You may need to move on if that doesn’t work however.

I hate games, personally i find flirting immature. If i like someone i let them know, if they like me i expect them to make an effort and let me know.

@tuxuday – I don’t think that @germanmannn ‘s story was too long.