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I’d say don’t do it. Like you’ve said what if things don’t work out? There are lots of women out there, don’t make it more difficult for you. Even if things work out spending so much time with her can be a pain in the ass too.
The place where I work don't allow couples to work together (yes for real) so it's not really a problem.
And honestly, the "what if things don't work out" is not my way of thinking

. I am more looking for routines that are not too hardcore and that can not make things too akward if she's not so interested after all
confidence is certainty,
you want routines that make you feel certain because you are feeling uncertain, just trust yourself, you want to ask this girl out, just ask her out, make up your damn mind about what you want
forget lines and gimmicks, think of attraction just as likability, if she enjoys being around you, you have attraction, if she knows who you are and feels like she knows you, you have a connection
don't over complicate it too much, if the attraction is there you don't have to do or say anything to keep it there, simply remain congruent and it will remain consistent
incongruence will kill the attraction, as soon as needy tendencies take over and you start changing up the game plan and acting in a certain way that is not congruent with what attracted her in the first place, this is when girls lose interest
and ironically it is really easy to get attraction and often guys cock block themselves more then anything, girl is already interested, just believe it and go for it, it's only a matter if finding out if she is available to you as well as attracted
if you have compliance for a meetup then you know you have something to work with, before you invite a chick out though you should have at least some rapport and a mutual interest in the activity that you plan to hang out and do
soc-psych-amp-pu-overjustification-amp- ... 21096.html
^ it's interesting that this post was revived today, it is fairly relevant to your post, don't fall into the trap of over gaming a chick and looking for that approval, if you feel you already got the approval, then trust yourself, you already got the approval, just believe in yourself
GOOD LUCK