Such a good question. I think that reading people’s body language is key. If I want a date to kiss me, I will show all the textbook signs (i.e. turning to face them, leaning in, solid eye contact…) I think if either party sees these signs and the date is going well, give it a shot. Hell, a kiss on the cheek is enough to test the waters. The nice thing was that my date kissed me 30 minutes into the second date. It was quite adorable and I was beyond relieved!