Should I ask her out?

Thoughts_Arrive

I've known her for a long time but haven't seen her in a very long time.
Only contact we have is occasional Facebook chat.
She invited me last year to a dinner she organised but due to falling out with some of the other guests I didn't go.
Last year when she invited me she said it's been a long time since she's seen me and thought she'd invite me.
I kind of got a feeling all these years she had a crush on me to, just some of the things she would do....
I have always had a crush on her but didn't go further because am/was friends with her brother (he's kinda disappeared so not sure if he is mad at me and doesn't want to be my friend no more) and going out with a friends sister is a big no no.

Should I just take a brave chance and ask her via Facebook if she wants to catch up over coffee?
Or should I wait until we chat next online and ask her then instead of just randomly messaging her online?
Would it be creepy just to message her when she isn't online?

rollings

Thoughts_Arrive wrote:

I've known her for a long time but haven't seen her in a very long time.
Only contact we have is occasional Facebook chat.
She invited me last year to a dinner she organised but due to falling out with some of the other guests I didn't go.
Last year when she invited me she said it's been a long time since she's seen me and thought she'd invite me.
I kind of got a feeling all these years she had a crush on me to, just some of the things she would do....
I have always had a crush on her but didn't go further because am/was friends with her brother (he's kinda disappeared so not sure if he is mad at me and doesn't want to be my friend no more) and going out with a friends sister is a big no no.

Should I just take a brave chance and ask her via Facebook if she wants to catch up over coffee?
Or should I wait until we chat next online and ask her then instead of just randomly messaging her online?
Would it be creepy just to message her when she isn't online?

how often do you chat online?

rollings

on second thought, yes, and do it right now

Thoughts_Arrive

rollings wrote:

Thoughts_Arrive wrote:

I've known her for a long time but haven't seen her in a very long time.
Only contact we have is occasional Facebook chat.
She invited me last year to a dinner she organised but due to falling out with some of the other guests I didn't go.
Last year when she invited me she said it's been a long time since she's seen me and thought she'd invite me.
I kind of got a feeling all these years she had a crush on me to, just some of the things she would do....
I have always had a crush on her but didn't go further because am/was friends with her brother (he's kinda disappeared so not sure if he is mad at me and doesn't want to be my friend no more) and going out with a friends sister is a big no no.

Should I just take a brave chance and ask her via Facebook if she wants to catch up over coffee?
Or should I wait until we chat next online and ask her then instead of just randomly messaging her online?
Would it be creepy just to message her when she isn't online?

how often do you chat online?

Every so often, not daily or weekly.
If I see her online I will initiate the conversation, she is rarely on chat and when she is she is busy, she never initiates online chat so I doubt she is into me at times, confusing.
However she would always be happy seeing me in person. :?

peacefrompaul

Yep! Go for it!

Thoughts_Arrive

I've typed up my message but too chicken shit to hit the send button.
I've always chickened out in life when it comes to girls. :fp:
I guess that is what an anxiety disorder does to the mind.

the wolf

better to regret asking and her saying no, then to regret not asking her and never knowing.

peacefrompaul

Thoughts_Arrive wrote:

I've typed up my message but too chicken shit to hit the send button.
I've always chickened out in life when it comes to girls. :fp:
I guess that is what an anxiety disorder does to the mind.

You just asked her out to coffee for catching up right?

Hit the send button

the wolf

Thoughts_Arrive wrote:

I've typed up my message but too chicken shit to hit the send button.
I've always chickened out in life when it comes to girls. :fp:
I guess that is what an anxiety disorder does to the mind.

bullshit, hit that send button!

Thoughts_Arrive

peacefrompaul wrote:

Thoughts_Arrive wrote:

I've typed up my message but too chicken shit to hit the send button.
I've always chickened out in life when it comes to girls. :fp:
I guess that is what an anxiety disorder does to the mind.

You just asked her out to coffee for catching up right?

Hit the send button

Coffee or after work drinks seeing we work around the city or do something at a mall.

peacefrompaul

Thoughts_Arrive wrote:

peacefrompaul wrote:

Thoughts_Arrive wrote:

I've typed up my message but too chicken shit to hit the send button.
I've always chickened out in life when it comes to girls. :fp:
I guess that is what an anxiety disorder does to the mind.

You just asked her out to coffee for catching up right?

Hit the send button

Coffee or after work drinks seeing we work around the city or do something at a mall.

PERFECT

Send away

dimitrispearljam

the wolf wrote:

better to regret asking and her saying no, then to regret not asking her and never knowing.

Thoughts_Arrive

dimitrispearljam wrote:

the wolf wrote:

better to regret asking and her saying no, then to regret not asking her and never knowing.

I know I know, I always wonder I might miss a golden opportunity here, she is very attractive.

STAYSEA

Thoughts_Arrive wrote:

I've known her for a long time but haven't seen her in a very long time.
Only contact we have is occasional Facebook chat.
She invited me last year to a dinner she organised but due to falling out with some of the other guests I didn't go.
Last year when she invited me she said it's been a long time since she's seen me and thought she'd invite me.
I kind of got a feeling all these years she had a crush on me to, just some of the things she would do....
I have always had a crush on her but didn't go further because am/was friends with her brother (he's kinda disappeared so not sure if he is mad at me and doesn't want to be my friend no more) and going out with a friends sister is a big no no.

Should I just take a brave chance and ask her via Facebook if she wants to catch up over coffee?
Or should I wait until we chat next online and ask her then instead of just randomly messaging her online?
Would it be creepy just to message her when she isn't online?

Can you use GTALK? It's better. Green means GO.
My brother told his friends DON'T EVEN LOOK AT MY SISTER! I would ask your friend. Personally, I would never date my little brothers friends, I'm just polite to them. But, every situation is unique.

Thoughts_Arrive

Yeah it might backfire, her brother might want to punch my head in.
But he has known me for a long time, he knows I am no creep and would treat her good.
I am surprised she has been single all this time, she is 25.
I also didn't think a relationship would work back then, she is big on partying, I just want to settle down and do chilled out 28 yr old things.

the wolf

Thoughts_Arrive wrote:

Yeah it might backfire, her brother might want to punch my head in.
But he has known me for a long time, he knows I am no creep and would treat her good.
I am surprised she has been single all this time, she is 25.
I also didn't think a relationship would work back then, she is big on partying, I just want to settle down and do chilled out 28 yr old things.

Just do it man. For real, the brother will understand.

81

Pics?



I'd wait till she was online and then ask her then, but i would ask her.

Either way, no risk no reward.

Thoughts_Arrive

Only downside she is a RnB chick lol

Thoughts_Arrive

81 wrote:

Pics?



I'd wait till she was online and then ask her then, but i would ask her.

You think it'd be creepy if she wasn't online or..?

STAYSEA

ASK HER BROTHER, FIRST.

Siblings are honest and very direct, usually.

donnaruhl

Sound's to me that yuo're weighing out the odd's by explaining the why I shouldn't.I think Wolf was right, You'll never know either way unless you ask.It's all casual. Now had you asked her years ago when you had the crush on her it probably would have scared you for some time. So just hit send.

Thoughts_Arrive

donnaruhl wrote:

Sound's to me that yuo're weighing out the odd's by explaining the why I shouldn't.I think Wolf was right, You'll never know either way unless you ask.It's all casual. Now had you asked her years ago when you had the crush on her it probably would have scared you for some time. So just hit send.

Held onto how I feel from her for a long time.
Kept it locked in me.

Thoughts_Arrive

STAYSEA wrote:

ASK HER BROTHER, FIRST.

Siblings are honest and very direct, usually.

If it's just a catch up over coffee or whatever it's not like I am going out with her right?
If it were to go to another level then I'd tell her brother.

STAYSEA

I suppose Female opinions don't count.

:roll:

Just Coffee!
But The Bro is your friend... If it goes farther. Just ask him. She could be a flake?
Casual.
PM if it goes nutz

donnaruhl

Thoughts_Arrive wrote:

Only downside she is a RnB chick lol

You are telling us about the con's but you're not telling us the pro's. You need to weight this out in your own mind.
What do you have in common?

81

If the brother is sort of out of the picture, fuck him.

81

Thoughts_Arrive wrote:

Only downside she is a RnB chick lol

Who cares, this isnt about a wedding, its about going on a date

SD48277

Ask her!

iOnlyownMymind

I think I'm probably as chicken as you, but there's no harm in going out for coffee. I don't think I'd worry about the brother either unless he's super defensive about her.

the wolf

81 wrote:

Thoughts_Arrive wrote:

Only downside she is a RnB chick lol

Who cares, this isnt about a wedding, its about going on a date

This.

Thoughts_Arrive

STAYSEA wrote:

I suppose Female opinions don't count.

:roll:

Just Coffee!
But The Bro is your friend... If it goes farther. Just ask him. She could be a flake?
Casual.
PM if it goes nutz

I haven't spoken to her brother in over a year now, wouldn't say he's a friend if he's stopped calling me.
I didn't say your opinion don't count, I just disagree sorry.