How do I at least get a date with a shy guy when I am shy and full of self-doubt?
May 2, 2010 9:36 AM   Subscribe

I like shy boys and grumpy boys. I am shy. How to approach?

I am a 24 year old female who was in a LTR for a long time. Ever since then, I have had no luck in dating. I try to be outgoing and approach guys I find interesting, but none of the guys I have tried to talk to reciprocate.
I'm not a fashion model or anything, but I've been told by guy friends (of the type that I would date if they weren't my friends) that I am attractive. I dress well, and am in good shape. I think the problem is the combination of the fact that the boys I like tend to be shy, and I get my feelings hurt easily.
So, if I approach and talk to a guy I'm interested in, then they don't seem enthusiastic about talking to me, or don't ever come talk to me when I see them around, I assume they aren't interested in me at all. This has happened several times recently, and it's starting to make me feel bad about myself. The weird thing is that I've been flirted with a few times by guys who are more standardly good looking, but I get absolutely no love from the kind of guys I'm attracted to, kind of (pardon the labels) indie rock nerdy academic type guys. This might just be because the typical good looking guys are more flirty by nature, and flirt with any girl around.
Does anyone have any tips for drawing out shy/grumpy guys? Shy guys saying what kinds of things women do or say that make them interested in continuing contact, or ladies who have had success catching a shy boy's input would be helpful. General advice for how to talk to men is also good. One thing I can't do is just straight up ask a guy out who I don't already know well. Approaching men to talk to them at all was a big step for this scaredy cat.
posted by anonymous to Human Relations (22 answers total) 14 users marked this as a favorite
In one sense, it sounds like you're actually attracted to men who aren't interested in you. This could be a challenge. However, it sounds like the uncertainty is what causes you to get your feelings hurt. If so, try introducing some assertiveness into your method, if not your manner.

If it's really just a matter of breaking the ice with these guys, then go up to one and say hi, tell him you're really shy, that boring ken-doll-meatheads hit on you all the time, but you really like guys like him - that you have a thing for grumpy, shy, indie rock, nerds and ask him out on a date. Like "so, would you like to go out with me some time?"

If you ask him out, at least you'll get a yes or no and if a no, you can move on to the next grumpy, shy, nerdy guy until you get the yes.
posted by jardinier at 9:54 AM on May 2, 2010

Shy boys are sometimes mentally "blocked" from interacting with girls. It goes way back to middle school, or earlier. It's not like they'll take the hint and go from there. You pretty well have to do all the asking/inviting yourself. Try that. Be open with your feelings, but not aggressive. Keep in mind that it's a numbers game--approach ten boys you like, and you might get one or two.
posted by weapons-grade pandemonium at 10:01 AM on May 2, 2010 [1 favorite]

So why aren't you dating your friends?
posted by St. Alia of the Bunnies at 10:05 AM on May 2, 2010 [7 favorites]

I think this particular combination of personality traits / desired personality traits are why okcupid et al were invented, honestly. Go on a bunch of dates with people — they (the dates and the people) will probably all or almost all be terrible, but having that experience will probably get you past the "oh christ I can't approach guys I like" thing.

also, don't date rivers cuomo that never works out well yes yes like the schtick he's pulling is cute now but he'll still be like that when he's 35 and you'll end up writing an article about it and mefi will get into such a fight and just no. please. don't date rivers cuomo.
posted by You Can't Tip a Buick at 10:05 AM on May 2, 2010 [1 favorite]

Shy girl dating a shy boy is about as touchy as porcupine sex. As someone who felt like one of those boys back in the day, I would suggest you try to be friends first. You have common interests, right? Start there. Be aware that many of these guys won't be confident or mature enough to actually take the big leap -- you might need to to get used to making the first move. Just know that it's not you, though.
posted by Gilbert at 10:34 AM on May 2, 2010 [3 favorites]

I've always been extremely reserved around guys, especially those that I am attracted to, to the point where I think guys thought I was either asexual or a lesbian. Instead of flirting and acting interested in guys I'm attracted to, I was kind of scared of them and would get very uncomfortable in their presence. I had crushes on boys in high school, but I never got a date until I started talking to people online, and that wasn't even on dating sites. I ended up posting on message boards of things I was interested in.. not to get a date, but because it was an outlet for me. The result was I met guys who had at least a few common interests and we also got to know each other well over text, where I wouldn't have been comfortable talking about a lot of things in person without knowing the person well.

My current boyfriend is a delightful, grumpy introvert that I met online, and we've been together for a few years. I'm confident that we would've never started dating if I'd initially met him in the non-internet world, so I am thankful that I happen to live in the age of the internet.

Good luck. :)
posted by wondermouse at 10:37 AM on May 2, 2010 [3 favorites]

Speaking as a shy guy: I tend to assume that girls are not interested in me. It can be hard to tell if a girl is just being friendly or if she's wants me to ask her out. There's potential for embarrassment if I misread her, so I tend to do nothing.

(I'm fully aware that this is an irrational fear, because the worst thing that'll happen is that she'll say no and we'll both be embarrassed for a little while. Knowing that it's an irrational fear doesn't make it go away.)

If I was approached by a pretty indie rock girl, and I was sure she liked me, I would still be kind of terrified, mostly because it would be such new territory. I would be scared of being too enthusiastic and scaring her off, so I would probably overcompensate and not act interested at all. This is compounded by the fact that my brain tends to shut off when I'm trying to think of things to say to potential dates.

I would then go home and kick myself, overthink everything I should have said instead of what I did say, etc, etc.

All of this to say: they might be really interested in you, but might not be able to express it immediately under pressure. It's what being shy is.

So, two suggestions: I know you said you don't want to straight up ask a guy out. But would you be confident enough to give him a piece of paper with your phone number or (possibly better) your email address? That would definitely send the signal "I am interested in you," and it would give the guy time to think something beyond "this hot girl is talking to me what do I do what do I do?"

The other suggestion, as mentioned above, is online dating. OKCupid is a good site to try. Again, since people are there looking for relationships, there's no confusion over whether or not you're just being friendly, and it's asynchronous communication so the guy has time to recover from the Rudolph "She thinks I'm cute!" reaction.
posted by JDHarper at 10:50 AM on May 2, 2010 [6 favorites]

Register an account at; create an honest, unique profile with photos; do a search for men in your age range and location restricted to keywords "shy" or "introvert[ed]." Meet in person, have a normal conversation (you don't need to talk to us in some special way that's any different from how you'd talk to non-shy/extraverted people), and see where things go.

Gilbert's comment that shy/introverted guys aren't "confident or mature" enough to be capable of dating is pretty insulting and inaccurate. I assure you, we're capable of dating. But it can be harder to get things started if you assume that dating = being approached by a guy at a party or at a bar, or that the appropriate way to start a relationship is to be surrounded by lots of platonic friends and let the romance emerge effortlessly out of that environment. (Those are extravert assumptions, you see.) Using a website might not seem very sexy or romantic on the surface, but it makes the process of finding someone you're compatible with much more efficient -- especially if you're aiming for a shy/shy or introvert/introvert match. Some people might see this as somehow less "mature" or "real," but I assure you, the successful results (which are abundant) are just as real as any other relationship. And I consider the process of reading through profiles to find who shares your personality/values/goals/etc. to be a lot more mature than going to be a bar or party and hoping that men hit on you (probably based on physical attraction).
posted by Jaltcoh at 10:54 AM on May 2, 2010 [2 favorites]

Get to know each other slowly. Think turtles. Then ask if he wants to see a movie and give him your number. Yes, you need to make the first move. Good luck!
posted by Honkshu at 11:03 AM on May 2, 2010

Oh man, I feel your pain. Through my twenties when I'd complain about this phenomenon my platonic guy friends would agree and consistently allude to the fact the kind of sweet shy bookish dude I'd be into, who'd also be way into a girl like me, would be super hard to get with as they'd be way too shy to ever approach me or even talk to me if I approached them. So sad.

The only way I worked around this honestly was to form a foundation of friendship first and, when there was any room for chemistry at all eventually acting on it once circumstances were most conducive to such a move. I think a couple AskMe dating advice regulars--grumblebee IIRC for example--have described this as their only MO as well, where some folks pretty much never "dated" as pop culture would have it and instead just had friendships that eventually become more. And have mentioned that doing it any other way is completely alien concept to them. Yeah, that's me too. I have only ever wound up with guys I was friends with for a good long while with no romantic intentions first. It's really roundabout though, for sure. But if you're a certain kind of person socially, introverted and shy and slow to peel out, and are attracted to the same sort it can often be the best way, albeit most slow-going. You can't really hunt it down, it just sort of happens organically. But it can be so worth it, because you end up with your best friend who you can be absolutely yourself around, knowing you skipped all "dating meat market" vibes and found someone who wanted to avoid that stuff too.
posted by ifjuly at 11:24 AM on May 2, 2010 [2 favorites]

Seconding weapons-grade pandemonium- it is a numbers game.

I could have written your post 5 years ago- super shy and feeling the frustration that the guys I like are at home not out looking for me in some cheesy bar.

I joined Plenty of Fish after I googled 'Dating for introverts' because it was the first hit and it was free. I think women really have the advantage here- I got lots of emails and got to pick and choose. I even hid my profile because there were too many guys trying to contact me.

I went on a date every friday night knowing I was gonna have to kiss a few frogs before I found my prince.

When I found him it was all worth it- we've been married very happy 4 years. He's super shy, grumpy and I never would have met him if his extrovert buddies hadn't forced him to make a page on a dating site.

Good luck- I know it sucks!
posted by NicoleyDarko at 11:36 AM on May 2, 2010 [1 favorite]

I think it is easier to date shy guys if you start off doing an activity with them - like join a club or attend a function with them. I think shy guys like to have seen you before a few times when you ask them out to somewhere not very scary, like to bring a friend and have coffee with you and your friend or to the movies. I'm not sure about grumpy guys...
posted by meepmeow at 12:03 PM on May 2, 2010

What if you put yourself out into the places those guys are likely to be found? (stereotyping ahead...) Hang out at comic book stores, attend events there. Does the Physics Dept at the local college hold events? LAN parties? Ask all your mother's friends if they have a son in their basement. I'm partly kidding, but you get the idea.
posted by CathyG at 12:16 PM on May 2, 2010

Give them cookies.
posted by amtho at 12:21 PM on May 2, 2010 [3 favorites]

"I've been told by guy friends (of the type that I would date if they weren't my friends) that I am attractive."

Date them! They're your type, they're attracted to you, you're already friends -- go out for a couple of drinks with your favorite single guy friend and kiss him and see where it goes.
posted by Jacqueline at 1:00 PM on May 2, 2010 [1 favorite]

One thing I can't do is just straight up ask a guy out who I don't already know well.

This is not true. It makes you uncomfortable and you do not like it. That isn't the same thing as "can't."

The solution is to do that more and get more comfortable at it.
posted by Ironmouth at 3:27 PM on May 2, 2010 [2 favorites]

If the type of men you are attracted to are not approaching you and the type of men you are not attracted to *are* approaching you, it's possible you are not looking the part of who you really are somehow. How you dress, how you carry yourself, even the car you drive (or the bike you ride, whatever) can send signals. All of this goes out the window once people get to know one another, or most of it does anyways, but fact is that you're not even getting the chance to meet the guys you want to get to know.

I tend to like my hair either quite long or quite short. I've noticed that when I go from long hair to short hair -- which is of course considerably faster than short to long -- the social change (if that's the phrase for it) is often dramatic. With my hair cut short, more conventional types of women who wouldn't have looked at me yesterday are now saying hello and smiling, the therapists and painters and writers now walk right on by without a second look, seeking out that neurotic they so crave. And this even if I'm wearing the same boots and jeans and shirts; if I change styles of clothing (suit and tie, shined up black shoes) it's even a larger shift.

I don't have any idea if this is a part of what's going on or not, but it's the first thing I thought of.
posted by dancestoblue at 4:50 PM on May 2, 2010 [1 favorite]

Academic/nerdy guys love to talk about their projects/intellectual interests/hobbyhorses. If you can pretend to find their "thing" fascinating, they will find you fascinating.
posted by orthogonality at 6:01 PM on May 2, 2010 [2 favorites]

"Hi! You're cute."
posted by BusyBusyBusy at 6:33 PM on May 2, 2010

Is it just me or are there a lot of posts about joining okcupid? I smell Spam frying in the kitchen!
posted by InterestedInKnowing at 7:43 AM on May 3, 2010

The weird thing is that I've been flirted with a few times by guys who are more standardly good looking, but I get absolutely no love from the kind of guys I'm attracted to, kind of (pardon the labels) indie rock nerdy academic type guys. This might just be because the typical good looking guys are more flirty by nature, and flirt with any girl around.

Beware of separating guys into camps of nerdy vs. "normal". I felt like you for ages -- attracted to a similar type of guy and mystified as to why things never panned out. It turned out that this wasn't really my type after all. Intelligence is a huge turn-on for me -- I was right about that -- but for a long time I didn't see that I was drawn to a particular type of intelligent guy because he had other qualities that made him seem safe. I didn't have to worry so much about feeling socially awkward if the guy was socially awkward too, you know? I was just too afraid to stretch outside my comfort zone.

And I also had some misconceptions about the kind of guy who can easily approach a woman and flirt with her. Yeah, a few of these guys may be the "flirt with any girl around" type, but it's more likely that most of them simply think you're attractive, and they just possess the confidence to approach you that your shy guys don't have. Don't write these guys off automatically. Talk to them and see what you might have in common.

If you do pursue the shy, nerdy type, I think you need to be willing to take a lot of initiative without necessarily getting similar efforts in return (at least in the early stages). Also, you should talk to men you're interested in the same way you talk to other people -- just add a bit of flirtation. Make eye contact, smile, briefly touch his arm, etc.
posted by spinto at 8:52 AM on May 3, 2010 [2 favorites]

Academic/nerdy guys love to talk about their projects/intellectual interests/hobbyhorses. If you can pretend to find their "thing" fascinating, they will find you fascinating.

Ack! Don't 'pretend.' Find guys who are into things you genuinely find fascinating.

Alternately, find out if there's something you both find fascinating (e.g., he's a computer geek and you're a Shakespere geek (or whatever) but it turns out that you both love Star Trek (No bloody T, N, or G!))
posted by ChurchHatesTucker at 9:31 AM on May 4, 2010 [1 favorite]

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