So for the past year or so she's been giving clear IOIs:

initiating contact
face lit up like a christmas tree on approach
nervous
holding lingering eye contact
kino (touching arm, massaging traps)
getting visibly upset when i tell her she's not my type
flirting
returning emails/texts

now i have texted her once telling her to meet me outside a well-known supermarket during her lunch break at work to which she replied she didn't feel comfortable with that and i once emailed her suggesting we meet up after she finished work to which she replied i could meet her and her friend during her lunch break which led me to wonder if she was truly interested and playing hard to get or just stringing me along.

here is the story so far:

me(last night): hey, can i ask you something
her (this morning): ok what is the question?
me: actually, i'd rather ask you face to face. have a nice weekend and i'll see you next week.

how shall i ask her out?

Why does she refuse to meet up with you alone? Any idea if you've done something to creep her out?

Also, don't do that texting shit you wrote at the end of your post. That comes across as pretty weird. Keep things straight and to the point. Ask her to meet up with you for lunch one more time and if she gives you another bullshit response, move on.

i'm 15 years older than her. i think that might be an issue. lol.

i'm not sure i should be asking this girl out you know. i remember one time during a works drinks do she was shouting out in the middle of the high street how i was old enough to be her father (awkward!)and yet she continues to keep giving IOIs. thats why im getting so confused.

i was drunk when i texted her last night. it felt like a good idea then. when i sobered up it definitely didnt feel like a good idea hence why i put it off.

If you don't mind me asking, how old are the two of you? That would definitely be the reason for the creepiness. It's very possible you are misreading the IOIs. Honestly, I get half of the things on your list from female friends who I know have no interest in me at all past friendship. Be careful with how deeply you read into these things.

i'm 39 and she's 24. we used to have this work email relationship where we were emailing each other flirtatious and suggestive stuff. at one point we were practically emailing each other all day every day. but this could be just a power thing. attention feeding her ego kind of thing.

yes, possibly. she's quite a flirtatious creature. apparently 'flirt' was her nickname at school. maybe i'm just misreading things. she's already said she doesn;t see me that way and that she likes being my friend. but ive also tried backing off. thing is when i back off she always finds a way to seek me out. like bumping into me in the hallway at work, or volunteering to work late shifts with me alone when someone calls in sick.

maybe i should just leave her alone. there are so many red flags with this one you'd think it was a socialist convention!

here are the red flags:

i work with her
15 year age gap
sending me flirtatious emails/texts whilst already in a relationship (not trustworthy)
discovered her emailing another male colleague
when i make a move on her she backs away claiming we're just friends only to resume contact when i back off and give her no attention (attention whore)