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How to ask an acquaintance out online?

nogutsnoglory

Moderator
So there is this guy who I met two years ago when he dated this acquaintance friend of mine. I REALLY liked him looks and personality wise but couldn't make a move since he was taken. We did become Facebook friends. I haven't talked to him since but learned they recently broke up. I'm not concerned with my pseudo friend being mad since we barely have anything to do with each other and apparently my friend broke up with him because he wasn't the one in love.

How do I without being an awkward stalker just pop in and ask him out on Facebook?

I sent a message saying what's up but have no clue how to handle this. I'm so nervous but this is my chance.
 

nogutsnoglory

Moderator
I'm so nervous I feel like puking. I just don't want to be weird and out of nowhere having not communicated just ask him out. When he responds to what's up I need to figure a reason for messaging. Shortly after ill ask him out for something casual like coffee.
 

Kev

Senior Member
I am the absolute worst person I know to take 'dating' advice from.. but if it were me, I'd message something along these lines.. 'Sorry to hear you N X are split. If there is anything I can do... want to talk.. let me know' You have expressed concern, an offer to help, and it is low key. If that doesn't get the response you hoped for.. next message. "Well, I think X is a fool.. you're great". Again, no committal, nothing too overt. Just you trying to bolster someone who is down. If they don't get the hint... well, sometimes men are totally oblivious. I know. I happen to play one on here.. ;-)
 

nogutsnoglory

Moderator
I know I know he may just have seen it and intend to respond later. It's not a major thing to respond to though so I am not hopeful.
 

Jennifer

Adminstrator
Staff member
Location
SLO
Why not Skype first before asking him out instead? Get to chatting and get to know each other better might help break the ice.
 

nogutsnoglory

Moderator
Well we have already hung out, it's just been a while ago. I do think Skype is a good idea though pre any date set up through an online dating site. It helps to make sure the person is who they say they are and there is some chemistry before meeting for coffee or a drink.
 

nogutsnoglory

Moderator
I am the absolute worst person I know to take 'dating' advice from.. but if it were me, I'd message something along these lines.. 'Sorry to hear you N X are split. If there is anything I can do... want to talk.. let me know' You have expressed concern, an offer to help, and it is low key. If that doesn't get the response you hoped for.. next message. "Well, I think X is a fool.. you're great". Again, no committal, nothing too overt. Just you trying to bolster someone who is down. If they don't get the hint... well, sometimes men are totally oblivious. I know. I happen to play one on here.. ;-)
I like that way of approaching it. If it was in person I definitely would. Online is a little trickier.

Thanks for everyone's feedback.
 

Kev

Senior Member
Well, in the few months I have tried online dating... webcam/Skype may not be the way to go. I was... convinced.. persuaded.. to try it by a couple of women that I had chatted with online. Apparently... there are exhibitionists (I've heard from others that it occurs in both genders) who.. post an intro.. phoney of course.. start a conversation.. suggest the webcam thingy... then without being requested to... show off their various 'assets'.

In your case, it is different. This is someone you know. But, to anyone else who thinks it is a good alternative with a 'blind' date online.. you may end up wanting to claw your eyes out. Mind you, some exhibitionists are better than others. ;-) Just a caution, OK
 
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