Help me grow a pair and ask her out

So background info, i like a co worker but had refrain from making a move before due to workplace ethics. Now that my promotion is secured and will leave the firm in 1 year max, i want to make a move.

We are close irl (based on a mutual friend's observation) but we never really meet or text outside work. I previously made some attempt at texting, reply was ok but late, then i just cut off.

Things is i wont be seeing her for a month. No text from her or me as of today, day 2. After which, one week then i wont see for months.

Let's get down to business, how do i ask her out when she comes back:

Lead up: send some text about coming exam to keep convo, maybe once ir twice

On tbe day: go for lunch. If she eat with her friend, ask again the next day and if she decline, skip.

During lunch: chit chat about whatever, then:

A. Hey there is this (useless) thing you told me i should buy (long time ago). Im going there after work, wanna go with? (really no intention to go unless w her tbh)

B. Wanna have dinner/coffee some times (text book recommendation, but i didnt asked out for a few months, so might come off as sudden, or obvious)

C. Ask what she does on her free time (asked before, mostly play w friend/game/watch show, mostly dating stuff). Then follow up like B, same issue.

D. I like you. If unfavorable reply, state clearly that you dont need to worry about it, just want to let u know since i cant help it.

E. Starting D with some generic questions about her dating life, preference etc. (never asked before)



Submitted May 28, 2019 at 05:03AM

So background info, i like a co worker but had refrain from making a move before due to workplace ethics. Now that my promotion is secured and will leave the firm in 1 year max, i want to make a move.We are close irl (based on a mutual friend's observation) but we never really meet or text outside work. I previously made some attempt at texting, reply was ok but late, then i just cut off.Things is i wont be seeing her for a month. No text from her or me as of today, day 2. After which, one week then i wont see for months.Let's get down to business, how do i ask her out when she comes back:Lead up: send some text about coming exam to keep convo, maybe once ir twiceOn tbe day: go for lunch. If she eat with her friend, ask again the next day and if she decline, skip.During lunch: chit chat about whatever, then:A. Hey there is this (useless) thing you told me i should buy (long time ago). Im going there after work, wanna go with? (really no intention to go unless w her tbh)B. Wanna have dinner/coffee some times (text book recommendation, but i didnt asked out for a few months, so might come off as sudden, or obvious)C. Ask what she does on her free time (asked before, mostly play w friend/game/watch show, mostly dating stuff). Then follow up like B, same issue.D. I like you. If unfavorable reply, state clearly that you dont need to worry about it, just want to let u know since i cant help it.E. Starting D with some generic questions about her dating life, preference etc. (never asked before)
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