Should You Kiss on the Third Date?

Yes, if she is showing she wants it. By the third date a woman who is still coming is usually interested, and a kiss is a normal next step. If you have not kissed her yet, you are not too late, and you do not need a grand gesture. You need a quiet moment, a clear sign from her, and a simple way to ask that she can say no to.

This is the situation most men worry about, so start there. It does not mean you blew it.

It does mean the question is now open, and she may be wondering about it too. My view is that the man usually has to make the first move. A woman is judged more than a man for being forward, so she is often more nervous than you are, even when she likes you. If you wait for her to start it, you can wait a long time.

So the third date is a good time to make the first move. Not because a rule says so, but because waiting longer begins to look like you are not interested.

Two dates is enough time for her to know whether she enjoys you. Three is enough for both of you to wonder why nothing has happened. A kiss that comes naturally on the third date does not feel rushed, and one that never comes can start to feel like a message. That is not a rule. It is a reason to pay attention.

A cheek kiss at the end of a night can mean many things. It can be warm and shy. It can be her way of saying thank you without more. It can also be a test of what you do next.

Do not guess. Read the rest of the evening. If she held your gaze, touched your arm and stood close as she said goodbye, she likely welcomes more. If she turned her head away quickly and moved to her ride, she may want to go slower. Either way, what she does next tells you more than the cheek kiss itself.

• She sits close and stays close, even when there is room to move.
• She touches you back: your arm, your knee, your hand.
• She holds eye contact, and her eyes drop to your mouth.
• She keeps the talk going at the end of the night instead of rushing off.
• She laughs at your teasing and teases you back.

My other tip is that new men almost always underestimate how much a woman likes them. If you think the moment is on, it may have been on ten minutes ago.

When you are not sure, ask. coach calls verbalizing the kiss one of the easiest ways for a beginner. It works because it gives her a clear chance to answer.

• "I would like to kiss you. Is that okay?"
• "I have been thinking about kissing you all night. Can I?"
• A playful version that one of his students used: "Are you as good a kisser as you are a conversationalist?" Wait for her answer before you do anything.

A smile and a step closer is a yes. Anything else is a not-now, and you accept it with grace.

Do not try to kiss her while you are walking or while she is looking away. Wait for a quiet, still moment, standing or sitting close. coach says friendly calm and loud hyper energy are both wrong. You want a little quiet tension.

Pick the end of a drink, a pause in a walk, or the doorway of her building. Turn to face her, stay close, and let a second pass before you ask or lean in. Lean slowly enough that she can stop you.

Keep it short and warm. Smile and say something light, like "I have wanted to do that." Then end the evening on a high note. You do not have to push for more, and you should not. coach says there is no hurry as long as things are getting better. Walk her to her ride, say goodnight, and text her the next day. A short message is plenty: "Great night. Same time next week?"

Say "No problem" and mean it. Stay warm and do not sulk, and do not ask again that night. A woman who is not ready may need another date, or may be telling you she is not interested in that way. Either way, your calm reaction is what she will remember.

If she says no a second time, even after a warm date, accept it and move on. Pressure never produces a real yes.