Posted by: Miss Jones | May 29, 2009

The Shy Guy

shy guys

Dear Miss Jones,

So I need some advice. There is a guy that I have worked with for about 2 years now who has also been in some of my classes that I like. Yet I’m not sure if he likes me. He always says “hi” and he kinda seems to cheer up when we see each other in class or at work but I don’t know if he is just being nice or what. Also, I have recently found out from some of the guys that we work with (no I didn’t ask, they mention things when I’m around) that even though they give him a girls phone number and tell them he’ll call he never does and I know he doesn’t have a girlfriend. So I have been waiting to see if he’ll ask me out or something but nothing has happened.  So should I get up the guts and ask him out myself? And what do I do if he doesn’t like me? I haven’t asked him out yet because I have been worried about that and since we also work together. So what should I do? and how can you tell if a shy guy likes you?

Yours Truly


Dear Confused…

This is a hard one.  I often find myself interested in shy guys too.  Especially the older I get because sometimes the shy guys seem like the only “normal” guys left.  As far as I’m concerned shy guys are sort of the hidden treasure of dating because they really don’t have a lot of other problems/issues.  They really can still just be single because it takes a lot of courage for them to pursue a girl.  Ahhhhhhh, but it is the figuring out if they like you and getting them to ask you out that is the hard part. 

Here are a few suggestions from what I’ve learned from dealing with the shy guy. 

Shy guys are still guys and they still have hormones.  So even if a guy is really shy if he is interested in a girl he will eventually make a move.  HOWEVER, that doesn’t mean that as the girl we can’t help them out. 

Now, I’m not into asking guys out directly.  I guess I’m old fashioned but I think that our whole dating system is messed up right now because first of all guys don’t ask out girls enough so when a guy does ask you out you take it really seriously and you freak out start hearing wedding bells and then that makes guys not want to ask out girls until they are REALLY SERIOUS about dating so then people don’t date enough and don’t get to know each other on a casual basis and we’re all getting old and even more single.  Really, our whole dating system is a little constipated if you ask me.  And all those problems are just complicated when we throw in the whole “well maybe I don’t have to ask her out because maybe SHE will ask ME out” thing.  But that’s a topic for another whole post. 

Let’s just say that I think we should still give the guys the privilege to be the pursuers.  It’s more fun that way anyway.  Now I know that some people won’t agree with me on my whole girls shouldn’t ask guys out opinion, but it is just my opinion based upon past experience.  I do think you can invite guys to do group activities, go to parties, etc. but don’t make it too easy for him to settle right into “hanging out mode.” 

So, anyway, while I’m one for asking guys out on dates I do think, especially in the case of the shy guy, that it is okay to create situations where it would be easier for him to ask you out.  So basically, ASK HIM TO ASK YOU OUT. 

For example, say he’s talking about how he loves going water skiing and this is something you would love to try you could say, “Oh, I’d love to go water skiing with you sometime.  I’ve always wanted to try it and it would be nice to go with someone who really knows what they’re doing.  We should go this summer…” 

Then that gives him the opportunity to say, “well, actually I’m going this weekend, do you want to come?” or maybe “sure, that would be fun” and then maybe he’ll call you and maybe he won’t but at least you’ve 1)shown interest in something he enjoys but more importantly 2) you’ve shown interest in doing that activity WITH HIM. 

Then you leave it up to him.  Especially in your situation where you work together.  You don’t want things to get awkward.  But, do your part to flirt, make sure he knows that you like him without being too forward or pushy, and give him easy opportunities to ask you out.  And you can create opportunities to hang out with you and him and other co-workers outside of work so that he’ll maybe start to see you as more of a friend and less of a co-worker. 

Oh, and I think you tell if a shy guy likes you by paying attention to body language, eye contact, and his actions.  Make it SUPER easy for him to date you if he wants to and then really a shy guy isn’t much different than a non shy guy.  You just have to make things a little easier for shy guys. 

Anyway, I OBVIOUSLY don’t have all the answers as I am still a Spinster and besides it is hard to say without really knowing you and him and the whole situation.  But just be yourself, flirt flirt flirt, and give him easy opportunities to ask him out.  Make sure through your words and actions that he knows that if he asks you out he will NOT BE REJECTED.  Then he’ll get up the courage to pursue you. 

Blog readers, what do you think Confused should do?  Do you agree/disagree with me?  Share your ideas with us in a comment. 

Good luck out there everyone! 

Miss Jones


  1. Miss Jones, your analysis of the world’s dating situation is SPOT-ON! I had a discussion with one of my Mormon guy friends on that exact subject, and the answer I gave him was that analysis! There should be some group called “Bring back the 50’s” or “Dating is an endangered species” on Facebook, lol 🙂

  2. I think asking him to accompany you to a play or a musical or something of the sort is good.

    Being brave goes a long way.

  3. Or, if he’s not calling *any* girls, maybe he’s gay. Take him to that musical and see how things go…

  4. I was just searching for other’s comments on dating and found this site. I’m the epitomy of the shy guy, the prime example. I wasn’t sure if i wanted to post a comment on a girl’s site but since my type is the subject matter why not. I think flirting really is the key…if the girl flirts with me and makes it easy to ask her out (very importrant cuz were often scared to death of girls we like), then he’ll ask u out(if he likes you), if he doesn’t ask you out, he’s not interested…don’t leave him any doubt if ur interested. There’s plenty of girls i haven’t asked out, I need some hints. good luck…relax, things work out in their time.

  5. I was interested in a “shy” guy I had in my institute class. We had great conversations in and after our institute class and we always sat together. We even sat together a time or two at broadcasts. I invited him to do things but he seemed to always be busy. I knew one of his friends and they told me he was really shy so I should ask him out. Like a lot of girls I was tired of being the one to make the first move, but after deciding that I really like this one I called him up and asked him to a football game. At the football game I made sure to flirt, flirt, FLIRT!!!! always the key my friend. After the game he took over the date and asked me to go for ice cream and then as we were walking he held my hand. Shy guys may need that first initial nudge, so make sure the “know” you like them and then the rest is up to them. Not much else you can do after this. Luckily for me it worked out ;-D and I am now dating the “shy” guy!

  6. Clueless sounds like she is looking for clues in the way that girls give them out, not guys.

    This guy sounds legitimately shy, or gay. Stick with the former unless he tells you otherwise. Miss Jones gave great advice in saying to basically ask him to ask you out, and you have to do it in person.

    Do not just ask him, “So when he taking me out?” That boldness will not get you anywhere with shy guy.

    Shy guy needs to feel more manly. Help him do this by letting him know that you would like to do something with him specifically. Help him by encouraging what, where, and why. This will let him be the man and plan how and when.

    What: what you’re doing on date (water skiing)
    Where: location (on the lake)
    Why: because you mentioned you would like to try it with him and let him teach you.

    When: you gave time frame, he decides particular date of. (this summer, July __)
    How: how he asks you out. (in person)


    Lucious: “They said you were a giant. They said you could crush a man’s skull with one hand.”

    Maximus: “A man’s? No. A boy’s”

  7. I would only like to add few more tips:

    Offering help – If the guy offers to help you with something, like really excitedly “Hey, I can help you with that!” that is also a sign that he likes you. He wants to do something nice to you, to help you out, it’s also pretty obvious – no?

    Carries on conversation – Have you noticed that he sometimes wants to just extend a conversation that has led to a dead end? If he really doesn’t want to end the talk and comes up with new topics, ideas, jokes, and if you determine that he does it deliberately – you’re right – HE LIKES YOU 🙂

    Not mentioning other women – This can be a pretty clear giveaway. If he normally talks about women and mentions his female friends but when he talks to you – he doesn’t – then that can be a sign. Why does he do that? Well he just does not want you to think that he might like any of those girls… It’s weird, but guys do it subconsciously…

    Well those are SOME of many signs if a guy likes you, but if you wanna know more, there’s a whole website covering the topic of how to tell if a guy likes you, so check it out –>

  8. Wow, interesting. As an ex-super-shy guy (sadly I’m now a slightly-shy guy with issues!), I’d say that quite simply what shy guys lack is confidence. If they really like you they will normally find that confidence from somewhere *eventually*, but if you’re not prepared to wait that long (and years is not out of the question here!), then you’ll need to lend them some, and as has been mentioned, making it clear that they won’t be rejected should do the trick.

    Confused mentions the guy getting numbers from his friends and then not calling. I’d be careful about reading anything into that. It’s likely that the friends were trying to matchmake and making promises without reference to him, leaving him totally freaked out.

    Anyway, I wonder what happened…

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