They absolutely flirted! You’re right about plays and poems being some of our best evidence: you might also want to look at Ovid’s Ars Amatoria (The Art of Love) which is a pick-up manual for both men and women, and has some hilarious advice on making yourself more appealing to the person you’re trying to woo. It talks about where to meet girls (the theatre or racetrack are good places, he says) and how to bribe her maid to tell you about her and take messages back and forth. Sometimes a man should weep and beg the woman; sometimes play hard to get, “there’s diversity in women’s hearts: a thousand minds require a thousand methods. One soil doesn’t bear all crops”

Despite overall low literacy rates, Ovid does assume his reader’s girlfriend can read, and advises flattering letters.

At parties, if you find yourself sitting next to the girl you like, Ovid says, don’t drink too much, but whisper to her, and let your hand brush against hers. And praise her looks.

He also talks about keeping yourself fit and well-dressed, with a good haircut and fresh breath - and the importance of remembering her birthday. Nothing has changed!