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How to make dating suck less

Expert-approved advice that’ll help you rethink romance.

Allie Volpe is a senior reporter at Vox covering mental health, relationships, wellness, money, home life, and work through the lens of meaningful self-improvement.

Popular opinion would suggest that budding romance in an always-connected, app-forward culture is, well, a mess. After all, dating has been described as a “minefield,” a “numbers game,” and “exhausting.” If you’ve been on a first date within the last few years, you may agree; you might even have a few horror stories you share at parties.

Still, dating doesn’t have to be a slog. It can be exhilarating and romantic, novel and affectionate, regardless of your age or dating history. Finding a partner doesn’t require a rigid strategy, but it could necessitate a change in perspective. Instead of viewing dating as work, take it as an opportunity to seriously consider what you want out of life — and who you want to spend it with. Ten matchmakers, communication experts, and therapists offer paradigm-shifting dating insights that might make you reconsider modern courtship.

Responses have been edited and condensed for clarity.

Don’t rely on only one form of dating to try to meet someone

“Create a three-pronged dating plan that includes online dating, meeting people in real life, and getting your ‘super connector’ contacts to set you up on good dates with people they know.”

—Bela Gandhi, dating coach at Smart Dating Academy and host of the podcast Smart Dating Academy

Take it slow — but not too slow

“Don’t linger online waiting for some magical insight to appear. If this person seems to have potential, get into a face-to-face context and start talking and sharing time together. But don’t be impatient. Sometimes very high-quality and long-lasting relationships can take off slowly and have a number of false starts and missteps. A rush to judgment has probably cost all of us at least one potentially good relationship in our lives.”

Chris Segrin, head of the University of Arizona’s department of communication and a behavioral scientist whose specialty is interpersonal relationships

Prioritize your dating life as much as your work life

“Put as much energy into dating as you do trying to build your career. It takes a lot to be successful. I mostly work with professionals and even I spend a lot of time investing in my career and my company and have to remind myself to do the same with my relationship.”

Daphney Poyser, matchmaker at Fern Connections

Let your 20s be for discovery

“The human brain does not fully mature until your mid-to-late 20s, particularly the prefrontal cortex, which is responsible for impulse control and decision-making. Statistically speaking, couples who get married at age 20 are 50 percent more likely to divorce than those who wait until they’re at least 25. Your 20s are for figuring yourself out.”

—Tennesha Wood, founder of The Broom List, a matchmaking firm for marriage-minded Black professionals

Use dates as an opportunity to connect with someone, no strings attached

“We often assume that love has to follow some grand romantic script and the only meaningful relationships are those that lead to marriage or long-term commitment. Of course it’s totally fine to pursue commitment, but it’s also okay to throw that script out the window. To make dating feel less like a slog to find ‘the one,’ you could reframe it as an opportunity to genuinely connect with someone you might not otherwise get to know. That connection could be friendly or romantic, physical or intellectual. It can last an hour or decades. I once spent a rainy afternoon trading dad jokes over beers with someone I never saw again. I was disappointed when we didn’t hang out again, but that didn’t change the fact that I’d had a great afternoon. The moments we spend genuinely connecting with other people make us, and them, healthier and happier humans.”

Mandy Len Catron, author of How to Fall in Love With Anyone

Do a chemistry test before meeting someone from an app

“Go on a video chat before each first in-person date to check the chemistry. Make it a must, because their potential unwillingness to video chat is communication too. I did this with each guy I matched with and it helped me avoid spending regrettable dates with complete strangers, or weeks of stilted chatting to find out we didn’t have the same values. Get on camera to introduce yourself, flirt, ask your hardball value questions, and set a date — or not — while live on the line.”

Joy Ofodu, host of the podcast Dating Unsettled

Have only one expectation on a first date: to enjoy yourself

“On a first date, do not ask questions to determine where they fit in your future, like, ‘What are you looking for?’ ‘Do you want to get married?’ The first date is only to establish if there’s a base connection. The question you ask is, ‘Am I having fun? Do I want to see them again?’

When you ask questions to see if they fit your vision, you objectify them as a means to an end to your timeline and the plan in your head. Looking for ‘the one’ puts a lot of pressure on you and the date, and that job interview energy can extinguish any chance of a flame. Also, you will prematurely judge them without actually getting to know a person. You don’t know enough about the person or know if you want to even go on a second date with them. You shouldn’t be trying to see if they fit in your future — it takes you out of the present.

I hear a lot of pushback from clients that their clock is ticking or they have no time to waste. That is a scarcity mindset and that can give off an intense or desperate energy on the date, which is a sure way to not go on a second.”

Amy Chan, founder and chief heart hacker of Renew Breakup Bootcamp

Focus on quality over quantity

“Be choosy. This may be a bit counterintuitive for people who like to keep their options open, but when dating it is really important to prioritize quality over quantity. This does not mean creating a long list of deal breakers. Reflect on the kind of life you wish to create with someone and the kind of qualities a person must have in order to create that life together. This will give you a more adequate depiction of who is a good match for you. The more you really sit with yourself and understand your actual desires for a relationship, the better you will be able to select the kinds of partners who align with the kind of life you want to create.”

Moe Ari Brown, love and connection expert at Hinge and owner of Transcendent Therapy & Consulting

Expect challenges and have support ready for when things get tough

“Embrace pessimism. People are often shocked by the amount of disappointment and anguish that comes with dating. Having an idea that things will likely be terrible before they are good helps to alleviate some of that stress. Expecting challenges means that you can also prepare for them. What support might you need if you get ghosted so many times you’re ready to throw in the towel? Who can you turn to when your date says something horrible like ‘I’m just not attracted to you’? These things happen, and they are awful. But planning for the worst will help you move through disappointments quicker. The trick is to not descend into thoughts like ‘It’s never going to happen for me.’ That’s fatalistic, and definitely not true.”

Myisha Battle, certified clinical sexologist and founder of Sex For Life LLC

Don’t allow your phone to become the third wheel on your date

“You may be tempted to check your phone if there’s an awkward silence, but you risk tanking the date if you’re staring at your screen instead of trying to connect. So my advice is to put your phone away and focus on creating those memorable first-date conversations that propel you into a relationship. If your date keeps pulling out their device, playfully call out this behavior and invite them to join you in a no-phones experience. For example: ‘I’ve been trying phone-free dates lately and it’s actually been a nice break for my brain. Want to see how long we can go without checking ours? First person to break buys the next round.’”

Logan Ury, director of relationship science at Hinge and author of How to Not Die Alone: The Surprising Science That Will Help You Find Love


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