Our Ten Favorite Dating Tips for Men

In all the years, after all the articles, these are the ten best bits of advice I’ve ever given to men who are out there dating women.

Get Clear on The Red Flags That Matter

There are red flags that are annoying, and red flags that are Molotov cocktails waiting to burn your life down. Treat each accordingly. A beautiful and kind woman with an annoying laugh may be tough on a long car ride, but at least she thinks you’re funny. Issues involving honesty, money, substances, entitlement, and kindness should have you running for the door.

Think, At Least a Little, About What You Need

Who are you? What do you like? If you’re a sports junkie who has season tickets to the Celtics, do you want a woman who hates basketball and wants you home every night? Too many times men end up with women who don’t like the life they cherish. This happens for two reasons: 1)She’s on her best behavior. 2) He isn’t self-aware enough to say, “I can’t/won’t ever give up my love of the Celtics. You okay with that?” Yes, you have to compromise some, but get the important cards on the table early and stick to them.

Be the Best Version of Yourself

Chances are, you don’t need to be anybody else to attract a great girl. There’s someone who will love you. But you may very well need to be the best version of yourself to attract a woman. Dress nice, bathe, smell good, ask lots of questions, smile, laugh, exhibit a little knowledge about something interesting, and most importantly listen to her. Just smile, nod and listen.

Do a Couple of Little Chemistry Checks During the Night

Not sure how the date is going? Do a chemistry check. While you’re standing together waiting for a table, for example, lean into her a little bit (Be subtle!) and watch what she does. Does she lean away, or god forbid, step back? She’s not feeling it. If she lets you lean in or even leans into you, things are going quite well.

If You Don’t Want to Really Kiss Her Two Hours in…

…there’s probably no love connection. I know that it can take women two or three dates to feel chemistry. We don’t work that way. You should really want to kiss her, and if you don’t, it’s not a crime. Just be nice and enjoy the conversation.

Crazy Never Gets Any Better

You know that thing about red flags that can burn your life down. Crazy is #1 on the list. Run at the first whiff of crazy. Don't make the classic mistake of thinking, "She's beautiful. I can handle the crazy." Trust me. You can't handle it.

Don’t say “I’ll Call You.”

Just don’t. If you don’t want to call her, it’s a cheap lie. She might believe you and then feel bad when you don’t. Even if you do want to call her, telling her is meaningless. Just say, “I had a great time tonight.” It will make you stand out from the other Joes who say it as a matter of habit.

Get an Assessment from a Female Friend

Dating is one of those things that we’re supposed to be good at with no practice and no detailed feedback. We just know when it works or doesn’t. The easiest way to improve your dating skills is to take a female friend to lunch and talk her through your last date -- your clothes, your venue choice, your conversation, your end of date approach. She will have opinions on all these things, and next time you’ll be better for it.

Do Whatever It Takes to Get Some Confidence

EVERY SINGLE WOMAN we’ve ever asked says that confidence is a deal-breaker when it comes to choosing a guy. If you don’t have it, you’ve got to go get some. It typically helps to practice just talking to women you don’t already know. (Join a meetup.com group, go, and be friendly.) But being really good at something that you can talk about is a shortcut to confidence. If you are a great snowboarder, she’ll sense your confidence as you talk about it.

Go Some Place You Feel Comfortable

Actor George Hamilton once wrote that when he goes to a new town he finds the nicest restaurant and pays a visit in the afternoon. He introduces himself to the maitre d’. He gives them his credit card and says, “Please take an imprint of this. I’ll be coming in several times over the next few days with various people. I’d like you to charge each meal, give yourself a 25% tip, and never bring me the bill.” Each night when he walks in with his friends the maitre d’ says, “Good evening Mr. Hamilton. Right this way to your table.” When dinner is done he tells his friends, “I’ve taken care of dinner,” and they get up and go. I know you’re not a movie star, but don’t lose the lesson. Whenever you can, date on familiar ground. You’ll feel much more comfortable.