Ask Out a Shy Guy?
The age-old question from a reader named kaizen: He’s not asking…should she? The answer isn’t always so intuitive unless you know what you’re looking for. Let’s take a look at her situation, and see what’s what:
Hi Jeff,
Just found your side today and I spent hours reading. I was googling my angst about asking a guy out and found you.
Aww, yeah. I’m always happy to grab angst by the lapels and slap the crap out of it.
A few months ago a manager at my gym started paying a little more attention to me than usual.He would try to strike up conversation with me.Kind of try to get closer,tell me I look nice or touch my hair and tell me its pretty.
Uh…rule of thumb. If a man touches your hair, and is not currently cutting or styling it,he’s at least interested in doing you. Or possibly checking you for lice, which only comes up if you work at a zoo and the “man” is a “gorilla.” In which case, you might look into some “therapy.”
It was only when he just joked to my personal trainer that he and I were flirting that I figured he might be interested. My personal trainer did a little digging and he told her that one day he saw me and thought I was beautiful. That’s all she got out of him.
Uh…again, rule of thumb. If that’s “all” you get…you at LEAST know he’s interested in some form of somethin’.
According to my trainer he is a shy guy who is basically inept with women and all of them at the gym give him a hard time about being single and that his behavior towards me was unusual.
I guess one would hope that a gym manager isn’t sprinting from woman to woman, touching hair like it’s going out of style. (Then again, it never really was in style, according to my information. Which I just made up. But I’m pretty sure it’s accurate.)
It was then I kind of developed a crush on him and started to talk to him a little more,I’m very outgoing and have no trouble talking to people.
Good for you. By your description, I’m sure you make him very, very nervous. In a good way, I’m saying!
It’s been a month now and he hasn’t asked me out yet. I dont’ know if he decided he didn’t like me or that he just wants to wait and see if there is anything more than a crush. One time I was playfully reading his palm and told him that he had a couple of serious relationships and he said he always has serious relationships.
He seems like a nice genuine person.
I’m so confused, I don’t know if I should ask him out. Oh and part of the problem could be that I’m going abroad for 2 months in the summer.
I need help ……
Dear kaizen,
Should you ask him out? Well, given what you’ve told me about him, I’d say that you should only ask him out if you ever want to, you know, GO out. Seems like he’s got his asker-outer stuck in park for some reason, and his co-workers description of him as “inept with women” would tend to imply that it ain’t gonna change anytime soon.
SO…WHAT TO DO?
Well, the way I see it, you have 3 options.
- Ask him out.
- Pitch him a MAJOR softball to try to get him to ask YOU out.
- Fuggedaboutit.
If you ask him out, I’d recommend going very low key. He’s already nervous, so let this be easy for him. Somewhere in the, “Hey, I was wondering — would you want to maybe get some coffee sometime?” area should do it. Done and done. And don’t worry about scaring him off, or whatever. If he likes you, you are NOT going to scare him off. And if he doesn’t, well, you’re not going to scare him on, either.
If you want to try to get him to ask you? I betcha a whole bunch of our readers have some insights into that sort of thing. I’m a dude, so I don’t really know how to do that. (If I want to go out with someone, I pretty much have to go ahead and do it. It just comes with the territory of owning a penis.)
And if you want to leave it alone and forget the whole thing, well, I have good news. You’re already doing it! Hurray!
Good luck, kaizen! Sounds to me like it’s worth a shot!
Ladies, a little help here? If you were kaizen, what would you do? How do you get the ball rolling with a shy guy?
Posted: August 12th, 2008 under Reader Requests.
Comments
Comment from mmagnolia
Time August 12, 2008 at 11:54 pm
Dear Kaizen: Here’s a little something for Your basket of prospectives.
Given that “going abroad for 2 months” option, give Mr. Sweets a raincheck-on OR ask Him for a *whatever* as a Welcome-Me Back when U return. Two months away should be enough space&time so that He can suit up with umbrella OR etch a raincheck 4U! He could be That Gem who’s worth Your everyWhile. Have Courage & Happy Prancing!
DeareeJM: MerciBouquets 2U……on behalf of the *We* who are non-”owning a penis” and who feel [in practical sense!] your point to “go ahead and do it”, albeit in a *girlie* fashion!
Comment from hunter
Time August 13, 2008 at 1:15 am
Ask the shy man out, see where it goes……I have had “soon to travel” women ask me out…….
Comment from mmagnolia
Time August 13, 2008 at 7:25 am
On 2nd thought, Dear ‘kaizen’:
Given His “serious relationship” business, U could try one of those *indirect* wiles [of course, for a friend of a friend--e.g., U].
Ask the Him exactly ‘How’ women could approach R have approached someone who is a laid-back, retiring [not! 2say 'shy'] fella. Even squeeze His arm as U ask. Ooooh Your LaLa!
Comment from Angel
Time August 13, 2008 at 10:25 am
I agree with Hunter – besides if you have an amazing couple of dates before you go, absence will most likely make his heart grow fonder…from what I hear, men fall in love in a woman’s absence …they like to miss us and fantasize about us- at least this is what I hear:) – best of luck!
p.s. I don’t believe in asking men out, but like Jeff says it all depends on the type of relationship and energy you want …if you do ask him out, I like the low key suggestions (I’m going..wanna come?) that way he still has room to be the pursuer (if that’s the kind of energy u like). And if u find that u continually have 2 hold his hand and lead him along, then I guess u have 2 decide if that’s the role u want to be in “forever”.
All the best!
Comment from Laura
Time August 13, 2008 at 1:48 pm
I’m not sure on this one. I think if a guy is not courageous enough to ask you out (um, if he’s not able to *get over himself*), he’s probably not worth your time. I’d say move on and get a real man. Nonetheless, if you’re curious, go for it! All I’m saying is, in my experience, when I have to make the first move, the guy just ends up not being that interested in me. Don’t expect too much. Plus, you might meet some hottie abroad!!
Comment from hunter
Time August 13, 2008 at 7:23 pm
to Magnolia,
..I have had my arm squeezed twice in my life time by two different women, I didn’t know, and I used to wonder…..now, I understand the message, thank you………..some of us guys and female body language, I am telling you…man can be blind as bats…
Comment from Melodramy
Time August 15, 2008 at 11:16 am
I basically agree with Laura. If you’re the one asking the guy out it’s because his interest level for whatever reason, is too low to actually motivate him. A motivated guy, WILL find a way to ask, even if it’s very low key and unrisky. I think if you have to start something with the guy because he just hasn’t, that’s the guy you’re stuck with forever after. He may accept your invitiations but still never initiate anything himself. But because you successfully went out with him at your behest, you will take that as more interest than it may actually be and continue to make ‘he’s so shy’ excuses. I think a guy who didn’t ask you first can go along for the ride forever saying yes to a woman who initiates and invites, without considering himself actually dating her since it didn’t come from him. I’ve seen it happen to my friends. I would find it hard to be satisified with a man that allowed things to start that way.
Comment from kaizen
Time September 6, 2008 at 7:04 pm
Thanks everyone!
I’m back form abroad. I did ask him out.We had lunch for 4 hours….talked a lot.It seemed like he wanted me to know exactly where he stands on a lot of issues.
After that I called him once or twice.He was busy one time and the next time he invited me to go with him while he visited his “little brother”.
I sent him a text message that I was going away and would like to spend some time with him.So, he didn’t ask me on a date but invited me to a work party that he was hosting. I went and he didn’t really spend all evening with me or anything but I was the only non work related or spouse /significant other of the people from the work place.I had a good time.Emailed him while I was away and he replied back.A very casual email (no “I Miss you” just said he saw someone who looked like me and thought I was back)
Anyway,I’m back and will probably see him tomorrow.I’m kind of thinking of giving up on this going anywhere.We’ll see.
Comment from Cassie
Time September 13, 2008 at 9:06 pm
I’m in high school and I’ve been friends with this one guy for almost a year. I really like him and I think he might like me too. All my friends agree. But hes too shy to call me or ask me out. What should I do?
Comment from Tracey
Time November 25, 2008 at 7:16 am
In the same boat girl,
I have a date tonight with almost the same scenerio. HOT guy, acts interested. I live in a small small small town. Seems every time I turn around this guy is there. He always speaks, smiles, comes up to me to talk. Resturants, grocery store etc. We have great conversation, do that eye flirting thing. I asked him out years ago, he said he was too busy. I asked him out again a week ago and same response. I told him, ok, you make time for what you are wanting to do. I’ve heard it all before , and walked off. He stopped me and asked me my schedule, called that same evening and has called every day since. We have a date tonight. Not sure how it will go, I’ll let you know…..He is one of those “I’ve been screwed around and no one will get close again guys”. Know what I mean? He keeps folks at a distance. Part of that I understand, he is in law enforcement and can’t let everyone know his business…..We’ll see how it goes….
Comment from tasha
Time August 12, 2008 at 6:18 am
Hi Kaizen,
Well does this man have a brother?
Anyway, if you decide that you want him to ask you out you could try a few of the things that worked with me in the past with a really really shy guy.
1) While talking to him after your gym session (and depending on the time of day obviously), you could tell him: “Im going to get some lunch/dinner/coffee do you want to join me”? The trick is being playfull and not making it sound like a big deal…so even if he says “no” you give off the vibe that you wont be offended. Pick a time when you know he could actually leave the gym and come with you.
2) Play the damsel in distress. You know him by now and his interests. If he knows about computers (like the guy I liked) you could say “my pc keeps crushing, I would like to buy a new one but know nothing about computers…” Hopefully he will get into “fix it mode” and will like to help. Even if he doesnt know about computers he will know about other stuff (cars, hiking, theatres…whatever) he can “fix” or “help you” with.
All the best and keep us posted
PS Im sure he is a wonderful guy but you probably dont know him that well. So if you follow the second option be safe and dont ask him around to your place to have a look at your pc (or whatever you chose). Keep it outdoors for a little while.