HELP! I’d Like the Woman I’m Dating to Be My Girlfriend, but What She Said Gave Me Cold Feet
Connell, here’s the situation. I’ve been seeing a wonderful woman for three months, and I was about to ask her to become my girlfriend. I’m crazy about her! But recently, she’s been talking about how she wants to get married before she’s 30. (She’s 27, I’m 32.) “I’m on the marriage track,” she said. That gave me pause.
I’m open to marriage, but I’m not sure I will be ready to get married in the near future. I need a bit more time than she does, I think.
I have two questions. If you become an official couple, are you basically promising a woman that you’ll get engaged? And how do I even know I should get into a relationship?
—Steven, 32, Denver
There is a difference between casual dating vs. a relationship. When you enter into an exclusive romantic relationship, you make several implicit promises, among them: be honest, be faithful, be supportive, and be kind. But you’re not promising her an engagement ring.
I think the bigger questions, Steven, are how to know that you’re ready for a relationship, and how to know that the two of you are a good romantic fit for the long haul.
To help, in my book and on my podcast, I discuss a framework that I’ll share here. When you’re considering entering into a relationship, your romantic situation will fall into one of four categories. Here they are, from worst (don’t do it!) to first (dive in!).
This is when a given woman is not a good fit for you, and you don’t want to be in a relationship with anyone. But perhaps you feel limited in your dating options, and you don’t want to be lonely, so you relent. This is the ultimate in settling.
When I was in my late 20s, I settled for the wrong woman at the wrong time, and our marriage was canceled faster than “How I Met Your Father.”
You’re ready to commit to someone, but the brutal truth is that you have a scarcity of choices, so you take for what you can get. This, I believe, is a majority of men.
You weren’t looking for love or a long-term romance, but how could you not make this incredible woman a part of your life? (As 80s pop icons Toto sang, “Love isn’t always on time.”) Many great relationships have begun this way, including my current one.
Brains, beauty, kindness—she’s the whole package. (And if she comes with a dowry, all the better!) She turns you into a human heart–eyed emoji. And you were already ready to dive in with the right woman. This is the ideal! (To paraphrase another eighties power ballad, “You’ve been waiting for a girl like her…”)
You seem to be in one of the top two categories, so this definitely bodes well for you and your (possible) new partner.
Do your two souls just dovetail? Do you deeply connect in ways both physical, emotional and in how you communicate? Listen to your gut and heart, umm, among other body parts.
Are you compatible in areas such as your core values, wanting a family, religious views, political beliefs, and, yes, getting hitched (or not hitched) in the coming few years?
Granted, you may only want a girlfriend for right now, not a wife or a soulmate for life. But I believe a relationship should have long-term potential. To make things work down the road, most of your Big Life Stuff should align.
Can you see the two of you growing together, complementing one another? If a relationship isn’t growing, it’s dying. That’s just the nature of life and love.
If you answered a firm “no” to any of these three questions, you may want to reconsider whether or not you should become a couple.
If you answered “Hell yes!” to all of the above, it’s a green light. Pop the relationship question.
(In a future column, I’ll write about how to have a deep, fulfilling relationship. Getting dates and attracting a girlfriend is one thing. Building a wonderful, lasting romantic partnership takes an entirely different set of tools.) But for now, I hope this has helped you consider if it's a good time to go from dating to relationship. If you have more questions, book a call.
On my last few dates, I got stuck in the so-called “interview mode.” I ask so many questions: “Where did you grow up? What year did you graduate? Where do you live? How long have you lived there?” And on and on. At one point, this one woman said, “I feel like I’m being interrogated on a TV show.” Yikes! So I want to ask you, how do I stop asking so many questions?
—Nick, 31, Indiana
Let’s grab a sledgehammer and bust a BIG dating myth. You may think “interview mode” is a bad thing, but it’s actually a good thing—as long as you’re asking her good questions.
Pummeling your date with a litany of boring, logical questions will get you breaking rocks while doing hard time in the Friend Zone. But when you ask her questions that are fun, flirty or thought-provoking (or even better, a combination of all three!), then interview mode becomes something that your dates will actually enjoy.
I’m saying that there’s real power in asking good questions.
Here’s a quick story from my dating past. I once had a first date with Becky, a costume designer who works on Broadway shows. I’m a natural introvert, and that night at the bar we went to, I didn’t feel especially “on” or charismatic. So rather than pretend and try to force gregarious energy, I decided to interview her, and let her do most of the talking. And she absolutely loved it. She opened up about her family, her quirky career and her favorite movies and TV shows. The conversational breakdown was about 75-25, in her favor. I was OK with that. I just listened and chimed in every now and then.
Here’s what shocked me. We said good night and I hopped into a cab. My phone buzzed before I got home: a text from Becky. “I had so much fun tonight!” she wrote. “You’re one of the most interesting people I’ve ever met!”
Me? Interesting? The truth is, I’d barely said a word about myself! But because I asked her good questions that she enjoyed answering, she found ME downright fascinating. As the old saying goes, “If you want to be interesting, be interested.” (Becky and I dated for a while and later became great friends.)
So, my point for you: Fear not interview mode. Just make it a great interview! To that end, here are 8 fun, flirty, interesting questions to ask on your next first date.
Ask this in the first few minutes of the date. The question injects small talk with some cheeky confidence. Give her a sly little smile when you say “besides meeting me.” You’re going for a playful vibe, not an arrogant one.
This focuses her on the idea of the two of you as a couple. Plus, it’s a more evocative, open-ended question about seeing the world, compared to boringly asking, “Do you like to travel?”
This question caters to your date’s ego, and the actress whom she chooses will clue you in on how she sees herself. Just be ready, of course, to answer your own question!
Everyone’s favorite word is their first name, so ask about hers. I once asked my date Faith this question and found out that she was named after the famous George Michael song.
Music is a fantastic first-date topic. Be impressed when she boasts about Beyoncé, or pretend to be shocked and horrified when she admits that it was…Nickelback!
We’re getting deep! This question takes your date back to an important day that she’ll love talking about, taking your conversation deeper than surface-level convo. It’s OK to get more real and deep as a date progresses. Be ready to share your answer before she does, to give her time to think on it.
This is an innocent, effective way to help spike romantic vibes in a G-rated way is to talk about each other’s first kisses. Again, be ready to go first.
OK, go back and re-read this list. Did you notice that the questions begin light and playful and become more personal and flirtatious? That’s by design. Emotional connection on a date should increase gradually and organically, so I’ve put these questions in the basic order you want to ask them. Though feel free to read the room and go with what works for you in the moment.
And they all lead up to this question, which tees you up to go for that first kiss. If her answer is, “I like to see a kiss coming,” then you can say, “Well, here it comes,” and move in to lock lips. If she replies, “I like to be surprised,” then you might say to her, “OK, then… surprise,” and make your move with as much confidence as you can.
Don’t fear asking questions. Just make sure you ask the right ones.
I’m an accountant, and I love the mathematical aspects of my job. There’s certainty in numbers and math. But when I go out to the bars to approach women, I almost never talk to anyone because it’s all so uncertain. What if she doesn’t like me? What if her boyfriend wants to kick my ass? What if I get humiliated? Is there, for lack of a better term, a formula I can use to make my accountant brain happy so that I can approach?
—Seth, 31, Long Island City, N.Y.
Seth, chatting up random women in a bar is very different than crunching numbers on your spreadsheet. Let go of certainty. Embrace uncertainty. You know the old saying: Nothing is certain except death, taxes and sucky Adam Sandler movies.
Connell Barrett is a dating coach for men who provides dating and relationship advice. He's been featured by top publications such as The New York Post and has appeared on shows such as Access Hollywood and The Today Show. He's also the host of the How To Get A Girlfriend Podcast. He'll help you learn how to meet and date beautiful women, and how to determine if you're ready for casual dating vs. relationship. Book a free call with Connell below.
I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!
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