How to Escalate Conversation with a Woman

Escalate a conversation by moving it up one level at a time: friendly, then playful, then romantic, and then a plan to see her. Each level should be a small step from the one before, and you should read her answer before you take the next. Do the same over text, with shorter messages and a clear aim, which is a call or a date. A conversation that never leaves small talk goes nowhere, and one that jumps straight to sex scares her off.

Escalating is not a trick. It is letting a conversation get more personal and more charged as it goes on. You begin with where you are and what you do. A few exchanges later you tease her about something she said. A few after that you say something that only makes sense between a man and a woman. Then you ask to see her.

Most men stop at step one. They keep asking about work and weekend plans until she gets bored. A conversation with no tension in it is the kind that ends with "great meeting you."

Friendly. Where do you live, what do you do, what are you into. This is where every conversation starts, and it builds enough comfort to let you move on.

Playful. You tease her, take something she said and exaggerate it, or give her a nickname for something she did. a dating coach describes the best version as honest: when she says something impressive, be impressed, and when she says something a little lame, tell her. It adds a bit of challenge, and she starts to work to impress you.

Romantic. A compliment that is about her as a woman, a line about how the two of you would get along, a mention of what you would do on a date. This is where she finds out you see her as more than a friend.

Go back and forth between levels. After a playful exchange, return to friendly. Then go playful again. Each return makes the next step feel easier, and a conversation that goes up and down feels natural, where one that only goes up feels forced.

a dating coach has a clear rule for texting that applies everywhere: do not escalate off a test or a negative. If she gives you a hard time, pass it with a smile and keep going. Do not answer with "let's get a drink." If she responds coldly to a joke, do not ask her out to make it up.

When she is in a bad mood or unsure of you, the last thing she wants is something more serious. Fix the mood first. Make her laugh, change the subject, wait. Then move forward.

Text is the weakest way to talk, and its job is to get you somewhere better. a dating coach's texting rules are a good guide.

• Keep it short. A wall of text looks needy and is hard to answer.
• One or two ideas per message. Do not stack plans, jokes and questions into one text.
• Move toward a plan. A call or a date is where the real escalating happens.
• Do not send heavy sexual texts before you meet. a dating coach calls this an inefficient move: it uses up her buy-in and risks turning her off, and it gets you nowhere. The same buy-in used on a date lets something real happen.

In practice, a good text conversation goes friendly, playful, a touch of romance, and then "let's get that drink Thursday."

Another point from a dating coach: if you and she have agreed to go to another venue, do not push the romance on the walk there. It is a short window, she may be nervous about where you are going, and a mistake costs the whole evening. Wait until you are seated. You will have more time, more privacy and more room for error.

Each step is a question, and she answers it with her behavior. Signs she is with you:

• She plays back when you tease her.
• She asks you questions and tells you things about herself.
• She leans in, touches you or moves closer.
• Her texts get longer or come faster.

Signs she is not ready:

• Her answers get shorter.
• She changes the subject when you get romantic.
• She stops asking you questions.
• She takes much longer to reply.

If you see the first list, take another step. If you see the second, stay where you are, lighten the mood and give it time.

Ask once the conversation has had a couple of playful exchanges and she is giving you real answers. You do not need a perfect moment. Name a day and a place that is easy for her, like a drink or a coffee. If she is warm, she will say yes or offer another time. If she is vague, keep the conversation going and try again a few days later.

Escalating a conversation is a series of small, honest steps, each one a bit more charged than the last. Watch what she does with each one. When the conversation has some tension in it, asking to see her feels like the next natural thing.