Hi Guys,

Mine is a bit more complicated then just the average date. Quick background, My best friend is married and I have gone on a few dates with his wife's younger sister. We went on a few dates about a year ago, kinda fizzled out because I went away on travel for a few months and when back nothing really happened and she started dating another guy. No problem, then they broke up and randomly out of the blue she texted me asking if I wanted to get lunch and go to a wedding with her. I agreed to both and we have hung out one time casually with my friend and his wife. All of which went well but still hard to gauge her intentions...The communication seems very one sided ( I ask her questions to time bridge, but nothing back, simple short answers which drives me nuts)

I am to the point where I would rather know if she just wants to hang as friends or wants to date and I am thinking of just asking her straight up.

I think the relationship could go either way, but since she is my best friends sister and I am close to their family I would rather ask then make a move and look like an idiot and avoid awkwardness in the future because even if things don't progress I will see her in the future at family stuff.

Whatcha guys think? Ask her straight up where she sees the relationship going? Friends or pursue a relationship? I'm having a quick lunch with her tomorrow so I think its a good opportunity

Don't ask her where the relationship is going. Her words and her actions are not congruent. Have you already kissed or tried to kiss her?

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No I have not kissed her or Tried yet. She just recently broke up with this other guy so I wanted to give her some time before rushing into it..

Main reason I wanted to ask her was to know whether or not to make the move for the kiss. Since there is more family stuff involved I'd rather not go in for kiss if shes not into it and be awkward for rest of time I have to see her.

What do you think?

She's getting a friend vibe from you as well I think. Things have been very formal between the two of you it appears. If there hasn't been any kino she may rightfully think that the two of you are just buddies. Asking her "where do things stand with us" is certain to stall out anything from happening.

When you meet, hug the girl. Gauge her response. Sit next to her at the lunch (not across from her). Go kino in a normal natural way on the lunch date. If you want a relationship, proceed in that way. Women are led by emotions, not factual statements.

Of course only go in for the kiss if she is responding favorably to your advances. Mystery's "would you like to kiss me" is always a great way to proceed here. Whatever happens, if you want something w/ this girl don't approach it logically. Women do not think factually and frankly it's a bit presumptions to ask the "us" question when there hasn't even been a kiss.

Women want lurid "love affairs", not pleasant tea and crumpets from their lovers. Keep this in mind. Again a warning: Since she may feel the two of you are only friends proceed w/ caution.

If you don't feel like laying it on the line with this girl, the solution is simple: just meet more girls.

Thanks Oceanx

I agree with your comments and will give your advice a shot tomorrow.

Do you think a Kiss is appropriate on a simple and quick lunch date? (Primary reason for the quick date is to see her again since I have been out of town and will be going back out of town after thursday)

I may feel it out and try to setup something better for maybe monday. Thoughts?

Think about it this way: Would you kiss your g/f on a quick and simple lunch date? Most likely you would. If you set the scene such that the girl FEELS like kissing, then kissing is the only reasonable outcome. However if you're getting full-on friendzone vibes despite your flirtatious manner I'd skip the kiss and probably next the girl altogether.
The ideal scenario is to get her to a private location where you can escalate properly.

Once again good point. Thanks

Ill give it a whirl and see. If it goes well, hopefully the communication improves. Tiring asking so many questions and trying to keep conversations alive if it is so one sided (no return questions)

Have fun and calibrate properly: She possibly feels she's meeting a friend for lunch and oftentimes the bridge from LJBF territory to 'sexual partner' territory is impossible to cross.

That's why the advice always is to go in as a possible sexual partner from the outset of any relationship, so the girl knows what category to place the guy in.

Maybe go in with an easy-breezy attitude, and the KNOWLEDGE that if this girl doesn't pan out there literally billions of others who would love a shot @ chilling w/ you. Try not to put your heart on the line - just have fun with it - nothing to lose.

One other point: You said that you will probably be seeing this girl at various things for the rest of your life. With that in mind, consider just scrapping the whole thing altogether and meeting more girls to avoid the permanent awkwardness you may experience around her from now on if she doesn't see you in a romantic light. Again there is an abundance of women out there.