Dating coach Connell Barrett answers your questions on third-date strategies, unlocking true confidence, and how to approach in a NON-creepy way.

After A Second Date, Now What?

I’m good on first dates, but then I’m not sure how to play the second or third date. I seem to lose a woman’s interest right before we start dating exclusively. It’s a problem because I’m 40 and I want to settle down with a great girlfriend. But I can’t get past date 3. After a second date, now what?

—John, 40, Los Angeles

Such a great question: After a second date, now what? I’ll bet you’re putting too much pressure on yourself on the third date.

The stakes are higher on date no. 3 because it’s the gateway to a relationship. Date 1 is about seeing if there’s chemistry and mutual attraction. On the second date, you get a sense for how comfortable the two of you are together. And on Date 3, you decide if you’re a good fit long-term.

Think of the first few dates like a series of job interviews: By the third, you’ll both know if you want the “job” of being in this potential relationship.

The stakes are higher, but you DON’T want to try too hard to be more impressive.

Repeat after me: To impress, do less. I don’t mean not to try. Just don’t strain too hard. Many guys feel the need to “up their game” on big dates—to plan elaborate activities or spend a bundle at a white-tablecloth restaurants. This can backfire because trying too hard conveys neediness. That kills romantic connection and attraction.

Don’t try harder. Go deeper. On the third date, try to connect over Big Life Stuff: careers, religion, wanting kids, politics, your core values. When you and your date find that your Big Life Stuff aligns, it’s easier to move toward becoming boyfriend-girlfriend.

Also, make sure that the woman you are dating feels a sense of progress—that every date is taking things further along.

There should be no rush to score, but you do want to be circling the bases. If there’s no physical connection by Date No. 3 (a good make-out, at least), something is off. Either it’s a lack of chemistry, or someone is not making moves—likely, you.

Many men get stuck on the same base for multiple dates. If you reached first base on date no. 1 and are still there two dates later, it can lead to the “friend zone.” The other person doesn’t feel things are progressing, so they lose interest.

In terms of physical connection, try to keep moving forward. The pace around the bases doesn’t matter. You can be Rickey Henderson or Big Papi. It’s all good, as long as you’re not stalled on first.

Crisis of Confidence

Connell, I feel so down on myself. I’ve only had one real girlfriend my whole life, and she dumped me. Most of the women I’ve been intimate with, I had to pay. I mean escorts. I’m so lonely, and sometimes I wonder if I’ll ever find someone who loves me for me.

—“John,” 44, Dallas

John, thank you for sharing in a vulnerable way. That kind of candor takes real strength, and I honor you for it.

I know exactly how you feel. I used to feel unattractive to women. Girls just didn’t like me in high school or college. And when I finally met the rare woman who wanted me, I married her—and she dumped me nine weeks later.

It was over so fast that we could have fought for custody of the wedding cake.

As I drove away from her house in my red Honda Civic—the backseat loaded with unwrapped wedding gifts to be returned for store credit—I felt rejected by an entire gender.

I would soon hit my low point. I paid for sex, too. I went to escorts and massage parlors. I was ashamed. In my mind, I was unworthy of wonderful women, so I had to pay them to be with me. While my friends were getting engaged and coupling up, I was in seedy hotels handing strangers envelopes full of cash, fearing arrest and feeling terrible—all for scraps of intimacy. My self-esteem was at rock bottom.

Finally, I said, “Enough!” And I went off on a decade-long path that transformed me from lonely and dateless to an international dating coach.

Here was the first step I took, and I want you to do it, too.

Take a sheet of paper, and write your “Awesome List.” Write out at least 25 reasons why you’re a GREAT choice for women.

To start to rebuild your confidence, you must get clear on what you OFFER women, rather than telling yourself bullshit stories of all the things you THINK you lack.

Don’t overthink this list. Under-think it! Any reason is good enough. Your 25 reasons should focus on ANYTHING, great or small, that you have to give. Maybe you speak a second language, or you can cook, or you’re well-traveled, or are a good son or brother. Perhaps you’re funny, smart, sweet, and have a good job or are working on getting a cool job.

Confidence comes from the inside. And guess what: Women LOVE confident men.

So write out 25 reasons why you’re a great choice for women, and you’ll notice how much better you feel when you focus on what you offer, rather than on what you THINK you lack.

Get writing!

How to Never “Run Out of Things to Say”

I get stuck in my head when talking to women, either on dates or out socializing. How can I keep conversations going in a way that women like, without choking under pressure?

—Kevin, 29, Athens, Ga.

How to not run out of things to say—it’s one of the biggest problems single guys face. “What do I say? What are the right words?”

Here’s what to do.

Make a shift. Lower the bar for how good your conversation has to be. You’re not giving a TED talk or doing a stand-up act. You’re talking to a woman. Your words don’t need to be amazing. They just need to be honest, authentic thoughts from the real you.

You likely think that every word has to be witty and clever, but you’re already cool and charismatic enough. You are already an authentic man of value.

So lower that conversational bar. In fact, I give you permission to be borderline boring. I’m not saying TRY to be boring. Just lose the “I Must Be Amazing” filter and let the words flow without overthinking them or judging them.

Free-associate and speak AUTHENTIC thoughts. If you’re talking to Super Hottie at the Party, and your mind is thinking, “Wow, she’s hot, and I’m kinda intimidated,” then THAT is what you say.

Tell her, “Hey, can I be honest? You’re just hot, and pretty girls intimidate me. Anyway…”

This kind of authenticity and vulnerability is mesmerizing to women because it’s rare, and it takes so much courage. Bonus: It will relax you because you’re not holding back. You’re putting your best, more real self on the line.

Don’t try to make your words perfect and amazing because it only creates tension. That makes it harder to connect.

You know who women find amazing? A guy who’s not trying to be amazing—rather, he’s expressing his best, most authentic self and thoughts.

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Connell Barrett is a NYC dating coach for men. He specializes in actionable advice to help men all over the world find their dream woman. Barrett's work has been featured in Maxim, Cosmopolitan, and more. Look for Connell's new book coming out Spring 2021.

Have a question? Ask Connell below!

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