"So, What Are You Looking For?"
Just because it's an important question doesn't mean you should ask it.
Relationship gurus Alison Armstrong and Julie Ferman tell women to ask men, point-blank, on the first date, if they’re looking to get married.
Instagram influencer Case Kenny advises women to ask men direct questions, such as: “What are you looking for? What does that look like?”
The idea behind this is understandable. The hope is that, by asking these important questions early in the dating process, he’ll give an answer that affirms that he wants the same long-term relationship as you.
If he doesn’t, you don’t see him any longer. Problem solved.
I disagree. Directly interrogating your date about your future may sound great in theory but it doesn’t work well in practice.
As an advocate for women, I completely understand the impulse to get the hard stuff out of the way quickly. No one wants to get hurt. No one wants to waste time. No one wants to invest in a dead-end relationship.
The problem is that leading with fear is not the optimal way to make a human connection. If a man did something similar, you wouldn’t find it attractive.
Take Tom, 66, divorced for five years, looking for a serious relationship, and confident he can get one. He is intelligent, financially secure, and dating casually. Tom’s glad to be free from a thirty-year loveless, sexless marriage and while he would love to get off the apps, he still hasn’t found “the one” yet. Like the rest of us, he doesn’t want to make the same mistakes he made in the past, so he ends his dates with an important question:
“Do you like giving oral sex? Because my ex-wife didn’t do that for our entire marriage, and I don’t want to waste time dating someone who isn’t into that.”
Is Tom’s fear - of going the rest of his life without a blowjob - unreasonable?
No. It’s perfectly fair to want to know that oral sex is available to him. The problem is that, instead of discovering your sexual proclivities over time, he asked you, point-blank, if you’d blow him regularly. Even if you LIKE oral sex, you’ll likely be turned off by the guy who asks for it like this.
In my opinion, this is the same as women asking men on the first date if they want to be married. And if you think I’m being ridiculous - comparing fellatio to marriage proposals! - let’s try a more direct comparison - a marriage-oriented man who wants to know his date’s intentions.
Steve is 44, never married, and desperately wants to find love and build a family. He’s cute, a good guy, and a successful lawyer, but he’s feeling the pressure of having to date someone younger and get engaged quickly. Steve has discovered that many women in their 30s are not in such a rush. They’re building their careers. They’re traveling. They’re “doing the work.” While they eventually want to get married and have kids, they’re not panicking about it.
After 20 minutes on Date 1, Steve dives right into Case Kenny’s advice
Steve: “What are you looking for? What does that look like?”
Jess: “Um, I’m not sure I understand the question.”
Steve: “Do you want to get married?”
Jess: ”Yes. Absolutely.”
Steve: ”When?”
Jess: “When I meet the right guy.”
Steve: “Does that mean in one year? Three years? Five years?”
Jess: “It means that I’m dating online, and if I feel a connection with someone, I’ll explore it and see where it goes.”
Steve: “But what does that look like? When would you want to have kids? How many would you want to have?”
Jess: “2, probably.”
Steve: “At 35, you’d have to start pretty quickly. So you’d probably want to be married in less than two years, right?”
Jess: “I guess…”
I was trying to be charitable to Steve and not make him out to be a crazy person. He’s just a guy with an agenda: find out on Date 1 what Jess’s long-term intentions are to ensure they’re on the same page.
How do YOU think this conversation makes Jess feel?
Do you think Steve asking Jess when she wants children makes her feel more comfortable?
Do you think this line of inquiry is fun for her and makes her eager for a second date?
Do you think she’s more attracted to Steve because he’s serious about relationships and she wants a man who is serious about relationships?
I do not.
Steve, despite his best intentions, just screwed up his first date.
When he asks for a second one and doesn’t get it, his story will be that women want to act all casual, date multiple guys, and choose the tallest, richest jerks who will invariably break their hearts.
What he will not consider is that he wasn’t a very good date.
Richard Wolman is a former Harvard psychology professor married to a matchmaker, Peggy Wolman. In 2016, we met on a Matchmakers’ Cruise and talked about this very subject. I found his take so fascinating that I asked him to email me notes from our discussions.
To build good communication, do not ask questions. Questions are a challenge or even an attack on another person. If you ask me a question, I have to think, “Uh, oh. What is the right answer?” or “What does she want from me?” or “Leave me alone – that’s none of your business,” and so on. A question narrows the field between you and the other person and shifts responsibility for the response away from the self. Even a simple question like, “Where do you want to go for dinner?” can be a way of saying, “I am going to put the responsibility for where we eat on you and not on me, so if it turns out badly, it is your fault.” (That’s one of the reasons women hate that question on a date – it puts the burden on them – a time-honored abuse of women.)
Of course, not every “friendly” question has such a dark side, but the impulse to keep oneself and one’s desires hidden is anathema to a quality relationship. So, “Honey, where do you want to go for dinner? can be replaced by, “Honey, I feel like Chinese tonight, what do you say?” She is then free to agree, or she can reply with a desire of her own, in which case you have a real conversation. These micro examples scale quickly to larger issues: “Do you want to come up to my place, tonight?” vs “I had such a good time tonight. It would be fun if you came up to my place to continue our evening.”
I shared the “no questions” idea with another dating coach who had a negative reaction. His rebuttal:
Being curious and asking questions demonstrates interest and is conversational. If a person's internal reaction to “What made you become an attorney?” is "what does she want from me? or that's none of your business," it’s a sign of an emotionally unavailable person. Only a defensive person reacts negatively to a genuine desire to get to know someone.
I agree with him - except that’s not Wolman’s point. Questions from a place of curiosity are great. Questions from a place of fear are problematic.
Good curious question: “Your profile says you’re a huge Red Sox fan. Was baseball something you shared with your father when you were younger?”
Bad fearful question: “Do you go to spring training and watch every Red Sox game on TV? (Because I want to know if you’ll be too busy for me)”
Good curious question: “I’m so sorry to hear that your Mom passed away. Were you close?”
Bad fearful question: “What’s your relationship like with your mother? (Because I want to know if you have a healthy respect for women)”
Good curious question: “How was the divorce emotionally on your family?”
Bad fearful question: “What’s your relationship like with your ex-wife?” (Because I want to know if she’s going to be a problem for me)
Do you see the difference?
A good curious question doesn’t have a “because” behind it and there isn’t a “right” answer. If your questions have a “right” answer, guess what? You have an agenda, he can tell, and he doesn’t like it.
As a coach for women who are tired of getting hurt and wasting their time, I know it sucks to hear this. You WANT to interrogate him. You WANT to have him fill out a survey by text with ALL the answers to your questions:
How much money do you make? How much do you have saved? How generous are you with that money?
Are you respectful of women? Or do you only value women for their looks and are largely dismissive of their emotional needs?
Are you good in bed? I know you think you are, but really, ARE you?
On a scale of 1-10, how emotionally available are you? Don’t lie to me. I’m not fucking around here.
Alas, that’s not how dating works. It’s also not how life works.
When my clients ask me how to know if a guy wants to get married, I ask them a question in return: ”How do you know if a guy likes fantasy football?”
They usually pause and reply, “I don’t ask him. He just tells me.”
And THAT is how you answer all these questions. They are organic. They reveal themselves over time, through repeated interaction and conversation.
If you dated me when I was 34, you would never have to ask me on the first date whether I wanted to be married. Sometime in the first few weeks of dating, I would volunteer the information to you: I had a great childhood, my Dad was my role model, I want to be just like him, and I can’t wait to one day coach my son’s basketball team.
If a guy DOESN’T EVER voluntarily talk about marriage, commitment, kids, or a future, what do you think that tells you? He’s not interested in it.
Does this take a few weeks to discover? Sure.
Is it better than scaring a guy off with your fear-based questions?
Hell, yes.
Your thoughts, below, are greatly appreciated.
What I Got Wrong
The wonderful Natalie Lue responds to last week’s piece, Why Are Women Embarrassed to Admit Love Is Important?
I don’t believe that my husband ‘completes’ me, but that doesn’t take anything away from either of us. I was raised in an environment of very ‘heteronormative’ and patriarchal notions about how women were incomplete without men, that *I* needed a man for security (actually said by my mother), and that basically you were nothing without the status conferred on you by first being ‘chosen’ by a man to be his girlfriend and then later his wife. I’d felt incomplete since childhood, partly because the first man in my life wasn’t around and I made that a thing about my worthiness. So I looked for men to complete me… and ran the gamut of going out with Mr Unavailables and a few assclowns. When I got into a monogamous relationship with myself, I met my now husband not long after. We’ve been together eighteen years this weekend. We have a blast together with our two teen girls and batshit dog. I’m know I’m doing life with exactly the person I’m supposed to be. A soul partnership.
I can also say that despite the wonderfulness of this, I’ve still had shit to sort out along the way because of childhood trauma and the impact of feeling unworthy. That’s no reflection on my husband or children; it’s being human. You can be happy and have the life you want and still sometimes grapple with feelings of not enoughness. Talking to clients over the years, a big source of pain has been the expectation that someone would complete them. When they then found themselves feeling ways they didn’t expect to once they were ‘complete’, they questioned the relationship, bailed, cheated, or blamed the partner or themselves and put too much pressure on themselves and the relationship. The moment life didn’t fit their image of what they thought ‘complete’ would look like, all the old feelings of being *incomplete* resurfaced.
There is nuance to everything. It means more when women say they’re looking for a man to complete them because of what is, quite frankly, a lot of trauma, programming and patriarchy baked into it. But there is absolutely zero shame in wanting a relationship, and women don’t need to settle for shite or pretend their needs or desires are otherwise just to fit the ideal version of womanhood that society fed them.
Your subheading says it all. “You can be happy single. But it’s okay to want companionship, too.” It’s both/and. There’s nothing wrong with desiring companionship, wanting someone to share your life with. It’s the *why* that can make it problematic. Not like we have to justify our reasons to ourselves, but wanting to share your life with someone from a place of knowing and valuing who you are is so very different from wanting to share your life with someone because you’re trying to fill voids.
As a white dude, I don’t choose to inject patriarchy and heteronormativity into my work, but I largely agree with Natalie’s both/and statement. Her emphasis is on personal healing and finding a partner from a place of wholeness. My point was that too many women have trouble admitting their deepest desires. Both are true statements.
Link That Made Me Think
Breaking News: Love May Not Actually Be Blind by Jodi Walker
Hollywood producers ask me every few years if I want to be on TV.
I generally say no because the kind of reality shows they produce are gimmicky and antithetical to the principles of Love U.
The author states the very ridiculousness of these premises:
“Yes, you have to get married at the end of this, but first, you have to get engaged to someone you’ve never physically met”; “Yes, you should marry your longtime partner, but first—live with this stranger you’re attracted to AND LET’S JUST SEE WHAT HAPPENS. Also, if you want to break up, you have to do it at a wedding altar in front of all your friends and family.”
The apex of this might be Love Is Blind, now in its sixth mind-melting season. Have I watched a single episode? I have not. But I don’t have to because I already know what’s going to happen. People who love each others’ personalities will VERY MUCH CARE about looks.
The show might as well be called “Duh.”
Concludes Walker:
Love is not blind. But it is—for better or for worse, for richer or for poorer, in sickness and in health—entertaining as hell.
On the Love U Podcast
Men Are About Feelings
While it’s easy to get mad at guys who overvalue youth and beauty, the truth is that you need more than looks to be with a quality man. In fact, quality men are all about how you make them FEEL. If your default behavior in relationships is to feel anxious and critical of your partner, it’s time to choose better men and make a big shift in how you show up. It’s a challenging concept but one that is very much worth your while. Plus, I tear up when I read a Valentine’s Day card from my wife, so that’s always fun.
My Not-So-Viral Social Media Post of the Week
You Can Also See Me On…
This week, I joined Beth Gulotta, host of the Quiet the Clock podcast. In addition to my regular takes about being open-minded about online dating and dating for character and kindness, we also address the pressures women face regarding age and fertility in the dating scene. Fun conversation!
You HAVE to Check Out…
TV - Scarlett Johansson as Katie Britt on SNL - Regardless of your politics, Britt’s rebuttal to the State of the Union was tonally odd and ScarJo gave a wonderfully weird interpretation. Saturday Night Live is hit and miss but this was a bullseye.
Movies - What We Do in The Shadows - If you like absurd comedy, this gem from Taika Watiti and Jemaine Clement (Flight of the Conchords) is easily the funniest vampire movie I’ve ever seen. Then again, I haven’t seen Twilight.
Substack - Why Kids Need Summer Camp - by Steve Baskin - Summer is right around the corner and our kids are perfectly content spending 10 hours a day on their iPads. Not on my watch. Get out of the house. Make friends. Do stupid things. Resolve conflict. Have an experience. Please.
The Honey Shot
I’ve prayed for God to send me the right person for as long as I can remember. I just knew He must have been up there working on something I wasn’t seeing. I heard a saying years ago that stuck with me. “God can dream a bigger dream for your life than you can”. And it was totally true!! I never imagined I would find someone so perfect for me and that I truly love with all my heart! Definitely worth the wait!
So, for all of you who are struggling, wondering where and when you will finally meet your person. I hope my story inspires you! If you want it, you’ll get it! You may just have to weed out all the rest before you’re ready for the one God has in store for you! Don’t put up with the games. And the biggest lesson I’ve learned… your gut instinct is always right! As Evan constantly will remind you in Love U: when you hear that little voice inside telling you something is off, believe it and listen to it!
If they are truly interested, they will show it. Don’t put your energy towards someone who isn’t showing up for you. Recognize it sooner than later so you can make room for the one who’s truly supposed to be in your life!
Tracey W.
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Loved it!!! I agree that men say what they want without asking. My friends often tell me to ask all those questions, but I place myself on the other side of the coin, and hate it when men do that to me. I run away!!
Thaaks Evan🧡🧡
Evan, I agree completely. Where we are coming from (a place of fear vs. curiosity) is everything! Tone is key. Intent is key. The middle way is a very good way ❤️Great piece, thank you!