lilfurson's Journal, 18 August 2011

Definitely take the first step on person! This way she'll see your confidence and will actually feel shy herself, giving you even more trust and power to look more attractive. Talk about anything - even if it's a stupid topic (the food she eat at lunch, the necklace she wears, or just tell her "you seem spaces out today" if she does, or whatever else), and if at any moment you find that you have nothing more to say or ask - smile, tell her that it was nice chatting to her and walk away. Next time she'll be looking for your face and hoping to chat some more. 

You work for the same company, is there any reason you would need to talk to her department for? If yes, the next time you need to deal with that department talk directly to her that way its work related, while your there you can just casually mention the weather (maybe lame but its something you know you both can comment on), or it there is a company function (picnic, golf tournament etc.) be like "hey are you going to the blah blah blah?" and go from there, its pretty amazing how it works. I do this all the time - infact today I used a tool audit as an excuse to go talk to one of the guys in the welding area where I work. Coming of more confident than you are is not a bad thing, and besides the only way to build confidence is to practice.  

Sadly I have no reason to interact with her in terms of work. I have never officially been introduced to her I only know of her through friends and what I've asked them. I'll try to come up with something but with never having talked to her or met her it will be a tough ice breaker conversation. 

Well that makes it a bit more difficult, I don't wanna just say "grow a set" because being a person who is quite shy I know that is not easy. You have mutual friends, use that to an advantage, maybe when she is talking to one of your mutual friends you can casually join the conversation, makes it a bit less awkward for both of you, once you do the initial contact - from then on is easy ;) 

I think that is a great idea. If one of your friends can help by talking to her, then you can join in. Then, you can stalk her a bit and find a time when you can run into her someplace other than lunch. Strange that she eats lunch with her ex ... but if you can have that initial contact, you can feel if your attention is welcome. My guess is that she has seen you at lunch and noticed you noticing her :) Coming up to her to talk will not be a surprise. You can alway use the line "Hey, don't you work in XXX department - Ive heard YYY is really god to work with" or something lame like that. Then you can talk about the weather or a ballgame or whatever...  

Maybe it's the romantic in me, but I find it cute and quirky if a guy finds a way to approach me and talk to me. Bonus points for being successful at it. Have your friends make a casual invite for lunch to join everyone together. Then you will have the opportunity to talk to her. You can do it!  

I would say just walk right up to her and introduce yourself (when she's not with her ex) Tell her that you would love to grab coffee, lunch, dinner, with her... Something low key. Just put yourself out there. I know there is that fear of rejection but I would rather be rejected than never try. You can do it :) 

Is this the girl you asked about a couple months ago? I think it was you anyway, lol. But anyway, if she's making eye contact with you, she definitely might be interested. I agree with the advice above, make the first contact in person. If you can't think of what to say - hmmm. You know, one of the sweetest things that happened to me: I was in a restaurant and this guy made eye contact with me a few times, and as he left, he dropped a rose he'd made from his straw paper on the table next to my arm and said, "Have a great day," with a smile and left. It was just so sweet. I had a BF at the time so I didn't pursue him, but it might me an ice breaker for you. Even if she doesn't say anything that day, you'll be on her radar... And you could use anything, a piece of candy, paper flower, something small and sweet but not creepy. You're a good looking guy, so you shouldn't seem creepy. :) Just drop it, and say something like "have a good day" or "happy friday" with a confident smile (remember, just fake it 'till you make it!) and walk on. If she asks "what's that for" you could say something like, "just for making me smile" Just a suggestion. :) Good luck!