You enter the comfort phase once she is attracted to you and you've convinced her that you are interested in her for reasons she thinks are valid.
In other words:
You enter comfort as soon as you both accept that you are attracted to each other.
You leave comfort (and go into seduction) as soon as you escalate to sexual touching.
Building comfort is all about helping to making her like you for who you are. Want to learn how to get her to like you and get the girl? Read on..
Comfort is the missing ingredient that allows you to convert mutual attraction into sex. Comfort changes her from "I want him but I don't know him well enough" into "I want him."
Sounds easy, doesn't it? By itself, it is. Most men can make a woman feel comfortable with them if they're not trying to have sex. (Sex comes in the seduction phase, so don't worry about sex for anything in the comfort phase.) However, you have three things working against you:
You never know how much comfort is enough. Not enough comfort before you shift into seduction, and you're a horny loser. Too much comfort before you make a move, and you're a pussy. This used to be a big trap for guys, but there is a way to work through this.
You can't focus only on comfort. If you spend all of your effort making her feel comfortable and safe around you without maintaining the tension and intrigue that you created in the attraction phase, then she'll get bored and you'll lose her. On the other hand, rocking the tension too high in comfort will feel awkward and out of place, and will also destroy any comfort you've built up.
You have to escalate touching. This is important preparation for seduction. In the seduction phase, you will obviously need to be touching her in an increasingly sexual way. You may have figured that this is seduction, and that you don't have to worry about physical escalation while in comfort, right? Wrong. It's hard enough in seduction to shift from non-sexual touching to sexual touching. It's infinitely harder in seduction to shift from no touching at all to sexual touching. You're setting yourself up for failure in seduction if you don't do the groundwork in comfort.
So, how do we build comfort and defeat these obstacles?
You get points for just being there: You build comfort with a woman by being in situations with her where you could theoretically try to escalate sexually with her, but don't. If she can sit on your couch without you being all over her, that will build comfort. If you can grind with her on the dance floor without grabbing her ass, that builds comfort.
Speed things up with multiple venues: Boy takes "Girl A" to the park. They have a picnic and hang out for 6 hours. Boy takes "Girl B" window shopping, then they grab a bite, then they go to bookstore, then they have a drink, all over a 6 hour period. Which girl is more likely to be "ready?" Girl B. She has seen herself in more situations with the guy, and therefore feels she knows him better.
Make YOURSELF her source of comfort: Imagine that a girl invites you to a party. It turns out that she knows "everyone" and that you know "no one." She leaves for a few minutes and you awkwardly meet her friends while attempting to make a good impression, but it's still stressful not knowing anyone. Then she comes back, and you're relieved. Then she goes and you're uncomfortable, etc. If you've been following along, you can see how useful this is in reverse. Bring her to places where you're the center of attention. Make her work to win your attention. By working to win your attention, by being happier when you're around than when you're not, by trying to make a good impression on your friends, she will be following behavior patterns that she is accustomed to following when she's interested in someone. Making her follow them with you solidifies her attraction, while building comfort.
Be genuinely interested in her. Remember, she won you over in qualification. You don't need to be so dismissive anymore. Now that you're in comfort, it's expected, normal, and attractive for you to ask her personal questions about herself. On the other hand...
Don't stop being a challenge. Keep the romantic/sexual tension going during the comfort phase. At appropriate times, you should still tease her, disagree with her, etc. Once there is no tension, the interaction becomes boring for a girl.
The comfort game requires a lot of subtlety and mental dexterity. The high-energy flair in attraction isn't really useful here. To some extent, comfort is where you "be yourself" – or at least, be who you want to be – and let her learn about you, while you do the same with her.
If this isn't easy, don't worry. Like the other phases, it needs practice and intuition.
Jealousy Plotlines! Use this one with caution. It's a necessary element in the toolbox of any man, so you will need to know how to do this effectively with 9s and 10s. However, this is a really easy place to make mistakes, so practice the basic elements of comfort first.
A jealousy plotline is used to make your target woman feel jealous of another woman, or women, who are interested in you and to whom you are neutral or interested.
You can introduce jealousy plotlines directly or indirectly. Here's a brief example of a direct jealousy plotline: I take Sarah out shopping, and happen to run into Amanda on the street. Amanda is quite attractive, gives me a big hug and a kiss on the cheek, and when leaving tells me to call her so we'll go out for a drink - it's a direct plotline because it's happening where the target (Sarah) can perceive it. An indirect plotline would be when out shopping with Sarah, I mention that I have to be done at 6, since a friend of mine is cooking me dinner. Sarah knows that guys don't make plans to cook each other dinner, so she knows it's a date - instant jealousy plotline.
Done properly, jealousy can do a lot of good:
First, it acts as a trigger for a woman's "pursuit" switch. A woman can be enjoying an interaction, not really thinking about it, until a feeling of jealousy hits. At that point, she can't deny to herself that she wants you. She'll try harder at that point, and in trying to seduce you, she will want you even more.
Second, jealousy is a strong feeling. Women like strong feelings and going through a range of emotions. Feeling jealousy and then feeling relaxed and then feeling confused and then feeling happy has much more of an effect on a woman than just feeling happy.
Third, jealousy will make your job in seduction much easier. She knows you have options, so withholding sex becomes counterproductive for her. She knows you can just get it somewhere else. Also, she knows that other women are staking their claim, so she'd better move on you before it's too late.
Fourth, jealousy can create comfort for a woman who dates a lot. Many attractive women are always casually dating a small number of guys when they are between relationships. A woman might find it more comfortable to date someone in the same situation as opposed to a man who is focused solely on her and who doesn't have other options.
This being said, nothing can totally kill a good interaction with a woman as quickly (and irreparably) as a poorly executed jealousy plotline. Here are some hints:
Less is more so don't overdo it. Let her imagination do the work for you. "I have to stop off and pick up some wine; a friend is coming over for dinner," is infinitely better than "my hot 21-year old neighbor is so in love with me, she keeps calling wanting to come over; it's really nice." The latter betrays insecurity.
Make it "accidental." Doing anything that makes it look like you're trying to make her jealous will backfire. Don't talk about another girl unless there's a reason for it.
Respect social norms. If you're on a date with a girl and you run into another girl, it's okay (good, actually). Introduce her to your date, and talk for 5 minutes. It's not cool to go off for 20 minutes with her and leave your date alone. This would display social awkwardness. Similarly, brushing off the "other girl" would make your date feel like you have something to hide. Greet the "other girl" like you would a good friend that you hadn't seen in a while. Take it from there.
Make sure the jealousy is warranted. If I'm on a date with Tammy the supermodel, bumping into my friend's dorky kid sister Gertrude and being all into her won't create much jealousy. You can help this - intro the "other girl" by telling your date cool things about her, the same way you would if you were talking to two women and your male wingman showed up.
Don't ever – EVER – be jealous yourself. She had a sex life before she met you. If you're attracted to her, other guys are too. Get over it. She will mention other guys, sometimes in passing, sometimes to test you. Don't ask leading questions (as an example: "Did he stay over?") or try to learn more (example two: "So, this guy you're dating..." in an effort to see if she contradicts you over the word 'dating'). Just cut the thread and move on.
It's important to develop a good intuition for different situations. Unfortunately, this only comes from experience. So get out there and try this stuff. Try it over and over until you "get it." There's no feeling in the world that's better than the first time you make a new tactic or skill work when picking up a beautiful woman.