What base is it when you’re flirting with a woman, and she… Commentary:When you hit the base where she checks if you're lost or just brave enough to try flirting 😂🚩 Related Funny Posts 🤝 Someone tongue kissed me recently in a way I can only describe as 5th base. I suck at flirting. I be like “is that so?” Not really into dating right now, but very into flirting, and that’s where things get complicated. “Boy, you made these perimenopausal ovaries come back to life,” – me flirting. Dating apps aren’t working, time to start drinking beer and eating hot dogs along the first base line at a baseball game.