.............. :( ! please help. no one answered me the first time.?

Question

theres this guy that works at the snackbar at my pool, and i
really like him. i work at the front desk and i see him all the time. ive
seen him look at me a few times and
he is the cutest thing ever. the thing is, he is painfully shy. he barely
ever talks to people that he isn't super close with,
and i really want to get him to open up. i'd talk to him but im
super shy too. ive talked to him before but its mostly when i place
orders for bagels and stuff. i really want to go out with him, but
that would require being his friend and im not really quite there yet.
we're just aquaintences, ive known him since the seventh grade. so i
was thinking of sending him a message on facebook like this:

hey ___,

i know this is like totally random and all, and i wouldve
asked you this a while ago. but i guess i was too chickenshit i never really
could cause we're always working. lol and i try to avoid awkward situations
whenever possible. anyway i was wondering;;; would you wanna hang out
one of these days? like maybe before school starts up?

well just let me know, i know its super random. whatever you say i
promise no awkwardness.i see you all the time at tuck so that would be no good! :]

-sara

how does that sound? i mean it IS super random cause we dont talk all
that much (seeing as he barely ever opens his mouth.) but i want him to be
comfortable with me you know?

my questions:
1. what do you think he'll say?
2. do have any tips on changing something in the message that would make him more likely to say yes?

thank you guys! you rock! :)

Answer 1

Congratulations on having the guts to make a bold move. I think he'll be happy and surprised.

Just two suggestions.

1. In your e-mail, you sound terrified. And if you seem scared, he'll be scared. If you promise no awkwardness, he'll be expecting awkwardness because he knows its on your mind, too. Take out about the parts about "randomness" because they make you seem apologetic. You don't need to apologize for asking someone to hang out! There's no reason to be sorry!

2. Recommend that you do something specific together. You'll need to think hard, but it'll be worth it. if you don't, a shy guy like him won't know what to do! He won't know how to respond. He might even be afraid of saying 'yes' because he'll be afraid that the two of you might end up just sitting around together in scared silence. An activity will give you something to talk about and it will take the pressure of him to be cool.

Shy people (at least in the beginning) need for you to take the lead. They need you to be confident enough for the both of them. Shyness is cute in small doses, but confident is always attractive.

Shy guys, just like shy girls, are usually waiting for a confident person to come rescue them.

Answer 2

If you've caught him looking at you several times; the answer will most likely be yes. Try whenever you order a bagel with something say oh and can i have you for a couple hours on Friday and then just smile? Even if he doesn't take you seriously at first then you have at least broken the ice. (make sure you grin or giggle when you say it so you can say you're just joking if you get nervous)

This way it's also just between the two of you and not out there for the whole world, that might embarrass him more. Try it, the worst that can happen is "no" and that is only a word. Good luck.

Answer 3

ok. first: dont say 'awkward' or 'random'. even in the message you sound timid and lacking self confidence. there would be a better chance of him saying yes if you put a lot less fluff in your message and sounded strong. thatd be especially good if he's shy also. take charge a little and things will fall into place more like:

hey-
got any plans for friday night??

seriously. short and to the point. and the first time you guys hang out is basically going to be a get-to-know-each-other thing anyway.
he will prolly reply with one of the following: "why?" or "nah sry" and if its the second answer then reply with "when are you free to hang out?"
dont be shy. especially if he is shy bcuz then nothing will be acheived. good luck!

Answer 4

honestly i know you are scared but straight forward is the best approach and has always worked for me. I say you need to say something to him in person. I would ask him if he would ever be interested in getting together maybe as a group first invite some other co workers out to calm the nerves and then talk to him while you are out. Sorry if that is not the type of advice you are looking for

Answer 5

I think that if he likes you, he will say yes. Afterall, you are just hanging out. There is nothing more that you could say to make him say yes. You did a really great job of writing that message - now send it!! Take a chance!!

Answer 6

Just send him the message or talk to him when he comes to your job. And i think he'll say yes since you have known him since 7th grade.

Answer 7

i think its good...but it would be much better to say it to his face...if u really think he likes u and u like him then i say go for it...let him know that u just want to hang out with him so u can get closer to him so u can maybe become boyfriend and girlfriend...hope i could help and good luck!

Answer 8

i think you should ask him in person.
Just ask basically the same thing you typed- do you wanna hang out sometime?