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
Confused….

 

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