Asking Someone Out

Visitor's Question from a 31-40 year old Male
If a guy asks a girl out on a date, and the girl responds
"i'll have to think about it..". How should he handle this
situation ? Bearing in mind that there is a 50/50 chance
that it can go either way.

There has been many instances where the same girl has been
seen staring at the guy, but has never made any attempt at
small talk (for almost 2 years ..!), and has been speaking
to almost everyone else in the office.

What are your thoughts on this most perplexing and odd issue ? Advice
It sounds like you lept into a situation rather than going into it slowly. You don't just walk up to a girl that you don't walk to regularly and say "OK we never talk but go out for an entire evening with me!" I think most girls would be rather hesitant at that!

Instead, your first step should be TO start small talk, and build it up into a friendship. Going out is about hanging out with someone you like and enjoying the evening together. If you can't even speak 3 words to the person in casual conversation, it's not time yet to be going out on dates.

So work on the flirting, work on the small conversation, and work on the friendship. When you're friends, if you guys work together, invite her to grab a drink after work! That is something casual and easy to do, but is also a non-work environment so you can be more relaxed together. The key is to take it in slow steps.

-- from Jenn
One of Your Friendly Advisors at

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