Vince Vaughn explains the awkwardness of dating best in the beginning of Wedding Crashers
Although this comedy eludes that avoiding the situation is better, what about those of us who do date? When is the proper time to make the first move or to kiss someone?
Subtle Touching: This is a great way to have someone read the situation correctly. Light touching, hand-holding, sitting close to someone, or making a point to be near that person can make the situation less awkward and more comfortable for both parties.
Formal Date: Once you take out the person on a formal date, this would be an appropriate time to go in for a kiss. Hanging out can be misconstrued, but if a girl or guy accepts a formal invitation for a date, it is a good indication that she would invite a goodnight kiss.
Ask and Tell: Let the person know you are interested if you are not great with physical cues. It is better to get shot down or share an awkward situation than it is to have the other person be taken by a guy or girl who can make a move.
The Two-Month Rule: Some people, especially women, like the man to make the first move. In today’s dating world we get caught up in hanging out and become too informal to read cues that would have been easily read if we were courting. A mildly aggressive nature is something woman tend to appreciate in men. After all, we want someone to protect us and look after us. If you have been hanging out with a guy and it’s coming on two-months without him making the first move, I’d cut your losses. The two-month rule will ensure that you are with a man who can take a hint and the wheel. If you don’t to cut your losses, it is up to you to make the move. If this is not in either of your natures, you are possibly going to have a hard time with open communication down the road.