shy guy in need of some advice for a date

[DividedSky]

Hey everyone, been a while since I posted on here but since my last few failed attempts I hadn't met anyone I was interested in until recently.

 

So here's the scoop: This isn't someone I just recently met I've known her for a little while and it happens to be my good friends little sister. I didn't have or at least notice any feelings for her until a few months ago, I had been unintentionally flirting with her for at least a month or so until one of my friends called me out on flirting with her. She's such a sweet, funny and beautiful girl and I really like her but part of my issue was the age difference between us as she's about 9 years younger than me. So because of the age difference and the fact she's my friends little sister I just tried to ignore it and do my best not to flirt with her. Well as it so happens I've come to realize that's just not possible.

 

So last week I finally worked up the nerve to ask my friend if he was ok with me asking her out. Obviously he was pretty taken by surprise but he said he didn't have a problem with it. At first he didn't seem to thrilled with the idea but he has warmed up (he's been giving me a hard time about it all week in a joking manner) and tell me it was glad it was me rather than some of the other people we work with. I guess I should mention the 3 of us all work at the same place, he and I work in the same department and a few months ago I got a promotion and I am now his boss. Not sure if that was worth noting as our friendship hasn't been affected by the change in roles at work.

 

This was doubly difficult for me because since I'm shy it was hard enough for me to ask him if he was ok with it, then I had to actually ask her out haha. Much to my dismay I found it very easy to ask her out (guess theres a first time for everything). And just like her brother I don't think she expected it either but she said yes, and I told her I'd talk to her one day this week about the details. And for me and my luck with asking girls out isn't that friggin sweet? Yea, well at least until today.

 

My plan was to not make the same mistake I normally do with girls and be too afraid to tell them how I feel and get stuck as a friend, and I was going to talk to her about that on the date. So I called her today to figure out what time to pick her up and so on. After we talked for a while she said she wanted to explain that she wasn't looking to date anyone right now and just wants to be friends for now. I told her that was fine but explained that I do like her but (and this is me being honest) that I'm not trying to rush into anything and would just like to go out a few times, talk on the phone some and see where it goes.

 

Shocker right?(sarcasm intended) If I had dime for everytime a girl I had feelings for just wanted to be friends I'd have more money than Hugh Hefner but I probably still wouldn't have the women lol. So anyhow we are still going out to dinner this weekend and I am now way less than excited about it. I'm sure I'll still have a good time but hearing any variation of a "just friends" line anymore just about ruins it for me.

 

So tell me am I doomed here? Am I once again trapped in the dreaded friend zone with no way out? Or am I wrong here, am I just being my normal pessimistic self? If I'm not doomed what do I do?

[camus154]

Cancel the date and save yourself some time, money, and mental energy.

 

You're already "friends" with her, so there's no point going out on some pseudo-date for the sake of being friends.

 

You're on the right track insofar as wanting to make it clear what you're after, but that's not something you should really have to spell out on a date with a woman. When you take a woman out on a date, she should have the common sense God gave a gnat to figure out why.

 

This is probably for the best anyway. Dating your friend's little sister who also happens to be a coworker....can't imagine what could go wrong there

[MasterPo]

I'm glad you took the initiative and asked someone out. I see problems with the brother/co-worker situation, I could be wrong but when those dating situations go bad people take sides and I don't see it ending good for you.

 

Since you have a date, might as practice and maybe she has a friend. She pretty much put the guns to you on the romantic aspects but you can network if you will through her contacts. I'm assuming you have honorable intentions, playing with her friends can also have consequences.