Romantic comedy (probably) I know the plot (sort of) Don't know the title. HALP

Hi. Please help me before I go mad.

Plot I remember certainly contains spoilers.
Release time - probably this century but I wouldn’t rule out late 90’s. Probably earlier than 2010.

So. There’s a guy that ends up with a girl in a city (details how, why and where vanished) and she puts him out of his comfort zones making do things that he wouldn’t normally do. (Again, no clue why) One such thing I remember was dressing him up in a fur coat and a wig with full makeup and drag him to some live tv recording for everybody to see. I think dressing up in latex and other such fun activities also had place but that’s speculation on my part.

Another concrete point I remember is that the girl dreams of owning a coffee shop/restaurant some day, she walks past the place she wants (currently empty) has name picked up, decor etc… but no money.
She shares with the guy about having such dream and the final scene goes along these lines: They part ways for some time only to meet again with the guy opening mentioned earlier establishment with exact decor and name she picked. She walks past the place once again she sees all of it and becomes (rightly so) very upset and rushes towards him. Moments later he tells her that he did it for her and she can run the restaurant/coffee shop now as she pleases.


I scoured the imdb plot dataset with no luck, google is starting to ask me whether I’m not a robot from the amount of similar searches per minutes I make. It’s time to ask the people. Someone must have seen it too!

An Awkward Sexual Adventure (2012)

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At first I thought you were thinking of After Hours 1985.