In this article, dating coach for men Connell Barrett shows you how to go from dating to relationship and how to determine if she's "the one."
My client Richard (Higher Self name: “Slick Rick”) had solved his biggest problem: not knowing how to talk to women. Now, he wanted more. He wanted a great girlfriend.
A real estate investor of Indian ancestry, Richard had only had one girlfriend by the time he reached his thirties. “In Indian families, you’re encouraged not to date,” he said. “You’re taught to focus on studies and career and somehow you’ll just magically get married. I never learned what women are like and how to flirt, and all these walls went up. I felt dysfunctional.”
Working with me, Richard razed those walls and found himself dating a few women at the same time. But having a “roster” didn’t fulfill him. He sought a relationship, preferably with Sarah, a kind, confident healthcare worker he’d had a couple of great dates with. But he wasn’t sure how to go about it.
“I was like, do you just ask? Or do I wait for her to bring it up? I wasn’t sure.”
I advised him to shift from Dating Mode to the Boyfriend Experience. That is, show the woman what a relationship with you would feel like. Basically, fake it till you make it . . . official.
Instead of going out for drinks and dinners, which they’d already done, Richard asked Sarah to pick out clothes with him at Urban Outfitters, attend yoga class together, and shop at Whole Foods. He introduced her to his friends and coworkers. He booked her for weekly dates. And soon she was reciprocating, asking him to join her and her girlfriends for brunch. “We both just clicked into these roles and it felt so natural,” he said.
Richard asked Sarah to date exclusively, and she said yes. Eight months later, while vacationing together in San Francisco, he dropped to one knee and proposed—in the shadow of the Golden Gate Bridge, no less. Another yes!
When you’ve found The One—or at least, the one you want to be your girlfriend—it helps to have a plan. In this chapter, I’ll give you the playbook to landing a great relationship. And I’ll share the three questions to ask your- self to make sure that she’s really the right woman for you.
When you enter a relationship, it will fall into one of four categories, depending on where you are in your search for love. Here they are, from worst to first.
Wrong Person, Wrong Time: This is when she’s not a good fit for you, and you don’t even want a relationship. But dating sucks, and you don’t want to be alone, so you relent. The ultimate in settling.
Wrong Person, Right Time: You’re ready to commit to someone, but you have a scarcity of options, so you settle for what you can get. This is most men, I believe.
Right Person, Wrong Time: You weren’t looking for romance, but how could you not lock her down? She’s awesome.
Right Person, Right Time: Brains, beauty, kind—the whole package.
If she turns you into a human heart–eyed emoji, and you’re ready to dive in. This is the ideal.
As men, deep down we all want true love, but we tend to settle for something comfortable and convenient. Something “good enough.” But when you settle, you miss out on finding the right person.
Don’t settle for “good enough.” This is too important. It’s your love life. Raise your standards and go after a truly great relationship with a quality woman who’s right for you.
If you feel like she might be the right person at the right time, you need to ask yourself three important questions before pursuing a relationship with her. There's no dating to relationship timeline. The most important thing to determine is your long-term compatibility.
Do your souls dovetail? Listen to your gut.
Are you compatible in areas such as core values, wanting a family, religious views, political beliefs, and cultural backgrounds? Granted, you may only want a girlfriend right now, not a wife, but a great relationship should have strong long-term potential. You may have stuff in common but to make it work long-term, you need most of your Big Life Stuff to align.
Can you see the two of you growing together, complementing one another? Because if a relationship isn’t growing, it’s dying. There’s no in-between.
If you answered “no” to any of these questions, there’s a chance you’re not with the right person. You may be settling. Remember, you’re a Radically Authentic guy with an abundance of dating options. Never settle.
If you answered “yes” to all three questions, then it’s time to give her the Boyfriend Experience.
Virtually all women want to trust their man. She likely won’t become your girlfriend unless she can trust you. Communicate openly, be vulnerable, listen, be consistent in your actions, admit your mistakes, and always tell the truth.
I met my future girlfriend Diana in a bookstore’s self-help section. Like many women of Asian heritage, she’s beautiful, but her bravery and sense of adventure is what wowed me: She’d just moved halfway around the world to start a new career in the U.S.
I wanted her to be my girlfriend, so for our second date, I invited her to sit in with my pub-trivia team, Trivia Newton-John. Why? Because pub trivia is awesome. (Fun fact: Blood donors in Sweden are sent a text when their blood is used.) Also, I wanted her to meet my nerdy friends and get a feel for what being my partner would be like. We were soon dating exclusively.
Introduce your potential girlfriend to your pals, coworkers, or even members of your family. Don’t have much of a social circle? Get on that! If you want to invite a woman into your awesome life, you must have an awesome life into which to invite her.
After a few “regular” dates, have her, say, help you pick out new jeans, join you at the gym, or go grocery shopping (followed by you whipping her up a delicious dinner, of course). Bonus: This breaks up the predictable, let’s-do-drinks model of dating and gives her some romantic variety.
Women tend to want to date guys who make them feel safe. This makes sense. Evolution selected men to be protectors. Unlike your Homo sapiens ancestors, you don’t need to spear a saber-tooth tiger to impress your partner. Just do some (nontoxic) manly stuff to give her that sense of safety. Such as...
Be fit. Women like muscles.
Catch the mouse or relocate the spider.
Start a campfire.
Change her tire.
Drive stick.
Be the one to lock the front door before bed.
Offer her your coat.
Place both hands on either side of her when she leans on a wall.
Assertively state date plans (“We’re doing dinner Friday at eight at that Italian place you like.”)
Carry her to the bedroom.
Oh, and fix stuff around the house. I’m no Bob Vila, but I once changed a date’s light fixture and before I was off the stepladder she was dragging me into her bedroom.
Be a good tipper—women notice that. And letting her know (in an unboastful way) about your charitable pursuits can be powerful, as Richard learned. “Volunteer work is important to me,” he said. “I donate to fight animal cruelty, and I work with the Ronald McDonald House [to help sick children]. I’d mention this to women and they’d turn to putty. Women really do like nice guys.”
The more often you see her, the more it feels like a real relationship.
After dating this way for a month or two, it’s time to make your coupledom official. Plan ahead. Make it a moment. Choose the right place and time to “pop the question”—say, during a relaxing day in the park, not in some loud bar.
Be sincere. Speak from the heart. Tell her how much you enjoy her and what she’s added to your life. (Should you use the L-word? Maybe! If you feel it, say it. If you don’t, that can come later.) Say something like, “I’m crazy about you, and the way you [specific thing you love]. I don’t want to date anyone else. I want to be your boyfriend. Would you like to be my girlfriend?”
If she says yes, celebrate, laugh, kiss, and rip each other’s clothes off. (If you’re in a park, wait till you get home for that last part.)
In the event she says no, it will sting. But listen. What are her reasons? Does she need more time? No matter what she says, be proud that you went for it.
When I struggled with women and started learning how to date, I thought that having a “rotation” would make me happy. It didn’t—not for long, anyway. I’m cool with dating around for a while, but sex without love and true connection is just candy for the ego. There’s a sugar rush but no real nourishment.
Dating to gratify your ego won’t fulfill you because it’s all about you. Romantic fulfillment comes from growing with, and giving to, a wonderful partner.
Read more about how to approach women and how to go from dating to relationship in Connell's book Dating Sucks But You Don't. Book a free call with Connell here.
Connell Barrett is an acclaimed dating coach for men who has helped men all over the world find the women of their dreams. He's appeared on The Today Show, Goodmorning America, Access Hollywood, and more. Listen to Connell's podcast on how to get a girlfriend, and book a free discovery call to see how he can help you.
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I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!
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