Adventure Dating

I have five rules for dating. They’re easy to remember, and can radically change your dating life, but before we get to the rules let’s take a look at one thing that most guys don’t remember.

If a woman shows up for a date then you’ve done well! She didn’t have to come. She made a choice to be with you that night. Have confidence that she likes you, and is at least contemplating something romantic. All you have to do is keep it from being an average date.

What’s the average date? Well, it’s something like taking a girl to a restaurant sitting behind a table and asking her interview questions all night long. You buy the dinner and the drinks and maybe walk her back to her place. You wait until the last moment before making a move and likely get rejected. Nothing exciting, nothing exceptional.

The seducer goes on adventures. Adventures can be wild, exotic, intriguing, and thoughtful. I want you to learn how to go on adventures with women; not dates. You and she are characters in a story and that story is exciting.

These six rules will help you turn dates into adventures and minimize possible mistakes:

RULE #1: Present Your Best Authentic Identity

Whatever venue you take your date should be a place that allows you to express your identity. In other words, the location you pick should allow you to easily bring up identity stories and share yourself.

RULE #2: Explore Multiple Venues

The more places you visit with a person the longer they’ll feel they knew you because you shared more experiences together. If you go boating and afterward to a cooking class, she will learn more about you than if you just go for dinner. Why? Because each environment comes with different sights and sounds, it generates new types of conversations, it suggests different things about your individual qualities, and at the end of the day, you’ll learn more about a person than you possibly could in just one place.

RULE #3: Ask Interesting Questions

You need to learn about each other, which means you shouldn’t be the only one talking. Be sure that you’re finding out what you can about the woman you are interested in. The questions should be relevant to the conversation. If she’s talking about her job, then think of questions that will reveal something about her. You’re looking to answer questions like these:

• Why does she do what she does?
• How does she feel about different aspects of her life?
• What kinds of things does she want to do in her life?
• What has she accomplished in her life, and how does she feel about those accomplishments?
• What stories does she have to tell?

RULE #4: Simplify Logistics

Before the date, always make a plan for where you’re going and how you’re getting there. Send the name and address of the location the night before the date via email or text message. If you’re planning on going from venue to venue, then spend some time planning out how you’re going to get to each place. Being stuck at a venue, standing outside trying to figure out how you’re planning to get somewhere can be a real mood killer. Also, dependent on the place you might want to let her know what she should wear. She’ll appreciate it if she is not going horseback riding in a cocktail dress.

RULE #5: Always Be Flexible

Sometimes you’ll end up somewhere that the woman doesn’t enjoy. That’s fine. Just be ready to move on and have a backup plan if this happens. That is another reason why I suggest going to multiple venues on your date. If they don’t like the place, you can easily move on and keep the vibe of the date positive.

RULE #6: Don’t make your move at the last minute

Most guys hesitate when it comes to going for the kiss. They wait until the very last minute, creating an awkward moment. Even if they manage a kiss, the situation is lack-luster. When you’re on a date and the opportunity arises, go for the kiss.

Note: Impatience and hesitation are not the same things. If you go for the kiss before she’s comfortable, you’re impatient. If you see an opportunity and chicken out, then you’re hesitating. Look for a comfortable window of opportunity to go for the kiss, and go for it. Take a bold romantic step forward.

Examples from students:

One of my students, a painter, would bring women to the arts district in Los Angeles. The streets there are covered in art painted by a variety of famous street artists. The arts district is also home to a number of hip bars and restaurants. They started their night walking the streets as he told her about the art, and what it meant to him. He talked about how he was inspired by the individual artists, while they barhopped from venue to venue.

Another student, in New York, used to take his dates to an improv show every Friday night. This particular student was a comedian and always liked to start his nights with a laugh. From there he’d walk with them to a local bar and then to a 24-hour diner. If everything went well, they’d end up back at his place, which was also in the neighborhood.

One of my favorite examples is from a friend who decided to build a pillow fort in his living room with a girl he’d met. Once the fort was built he made plans to go out for burgers at a nearby burger joint, with the promise of playing truth or dare in the fort once they returned. It wasn’t long before the game went from PG to XXX.

Should I buy drinks for a woman I’m interested in?

My advice is, if it feels like you’re paying for the woman’s time, don’t do it. You’ll feel used and she’ll feel obligated, which will drive her away from you. That’s what I tell my students when they ask about buying drinks when they’re out meeting women. Paying for her time means that she’s sticking around just because you’re paying for her drinks and for no other reason.

Don’t put yourself in that situation. Go ahead and buy drinks, but only if it’s the kind of situation where you’d buy one for a friend.

Try this: When you’re on a date say, “I’ll get the first round you get the next.” It’s something I’ve done with friends, and dates – it’s a great way to make paying the bill easy and comfortable.