What do I Do Next?

[ripcord1718]

So I'm a 23 year old male and I've recently been spending a lot of time with my friends older sister who is 29. We hang out every 2 weeks or so, going to trivia at a local bar and getting dinner and drinks every once in a while. We take turns paying. We have a good time non-stop laughter and what not and end up spending more time with each other when we hang out.

I'm having trouble kicking it up a notch though. She works early which puts a damper on things and I am kind of shy and have trouble advancing things. So I'm looking for any advice. Any help would be most appreciated. Thanks in advance.

[buni]

Just go for it ..seems like you are relaxed enough to hang out with her..so just casually slip it in there and see what happens.

[ripcord1718]

Haha I mean that's the thing. I am alright at flirting but I am absolutely the blindest person when someone is trying to flirt with me. And she is kind of a tough read. Sometimes it seems like she'll find excuses to like touch my hand to get my attention before telling me a story. And other times not. When we talk there is always eye contact and we end up hanging out longer than seems like we originally plan. I dunno, like I said, I'm an idiot when it comes to picking up signs. And I'm a titch shy also in situations like this.

[ripcord1718]

Many thanks. Yeah, I'm going to have to give that a go. Unfortunately we're both traveling the next two weeks for work so probably won't see each other for sometime. Much appreciated though.

[barocca]

While you're away traveling, send her some text message to show signs of missing her absence. Don't forget the gifts for her when you return, a simple token would do the trick.

[ripcord1718]

Oh. Good idea. Yeah I was thinking about texting her but I hadn't thought about gift. We both like wine so I could get a bottle perhaps. Or is that a little much?

[talkdate]

well, i think you are quite comfortable with her. so, just go for it.

(unapproved link)

[ripcord1718]

I just got back. I sent her a couple of texts asking about the college basketball team we both like. I also brought back a nice bottle of wine. How do I prop the question of getting together specifically to pop that cork though?

[ripcord1718]

We usually go out to eat, watch college basketball, go to DJ Trivia and a movie every so often. I've actually been out of town again recently for work, but we're doing DJ trivia tomorrow which is the first time we're seeing each other in a while....pre-game advice?

[houstoncougar]

for goodness sakes stop burning daylight here and when you see her just ask her straight out if she missed you and if she says yes ask her how bad and see what you get with that one!!!