What the hell does this chick do? She doesnt drink, she doesnt date, she doesnt let you take her out very often.... Sounds like a stick in the mud.

Dont worry if things dont work out.. I understand the "What if" thing youre going through, however if you go through life always asking "What if" youll drive yourself insane.

Things happen for a reason - If its ment to be it will be and just roll with it.

If you want to do this, ask her out.. if she turns you down then stop asking her out, stop giving her attention altogether. You can be cordial, dont be a dick.. but dont be the lost puppy dog trying to ask her out all the time.

If you get turned down again and stop paying attention to her, she will either chase you if shes interested and is just playing games (shes losing her own game if she chases you at this point) or she wont chase you... at which point you stop pursuing her altogether and stop wasting your time.

 

^You guys and your tactics.

Its pretty weird that she is 26 and has never been in a relationship but I think you should just ask her. Maybe you could say something like, "I really enjoy hanging out with you and I was wondering if you would consider becoming more than friends?"

She already knows the you like her, you've taken her out and paid for multiple dates. If she says no, I don't think it would make it awkward and maybe she'll start chipping in on the tab.

 

If you really wanna proceed, just keep doing what your doing. Ask her out and keep going on dates. You can always tell if your approaching the friends zone so do something that tells her other wise. Or even after a few dates, be straight forward and let her know you want her to be more than friends if there is a possibility. I'm pretty sure though after a few dates, the topic of relationships should come up and that is when you let her know.

IMHO, since she never had a serious relationship, plus she works with you, I would keep away from anything serious with her. Past experience, she will not understand alot of the concept behind a relationship and what it entails. I can see her going psycho if she's into you and might bring it to the workplace. Just saying.

 

Umm am I the only one who noticed this?

Hopefully this isn't normal to you guys...

 

Clawhammer,

You like who you like, and if you are interested I'd say give it a shot.

But I was in the same situation once or twice and thought the direct approach was best. Say, "Hey Matilda, I like hanging out and enjoy your company, but I'd also be interested in dating you. I thought I would be straight about it, so if you'd like why don't we go get some dinner or something, if not, we can just be friends." If she bristles, no harm, move on.

In each case it was like "DUH, the reason I keep hanging out with you is I am waiting for you to ask me out." Or she will say, "I thought we were on a date."

But if the time comes where you want to break it off, you have to be equally direct and honest or you get trouble.

 

Make a move.

 

 

Just go for it. Worst scenario, she'll just turn you down. Although, she sounds kind of lame. And I hate girls who don't at least offer to pay, esp. when on a "friends date".

 

Small update: tried to ask her out for this weekend, but she'll be out of town. We're probably going to do something the following weekend though.

 

ftfy