When it comes to second dates, there are generally two schools of thought. One being that–barring any red flags–you should consider going on at least two dates with someone to determine with certainty whether you’re interested. The other belief is the opposite: that if you’re not clicking on date number one, it’s okay to decline a second date and move on.
If you do want to see each other again, awesome! But in some ways, a second date carries more pressure than the first, because it’s when the real assessing of future partner material begins. “It’s more indicative of compatibility and potential for a long-term relationship,” says relationship scientist Marisa T. Cohen, PhD, LMFT. “First dates can be riddled with anxiety, even if you’ve met on an app and have been talking for a while. It’s also usually more of a demographic survey. ‘What do you do? Where did you go to school?’ Second dates are where you go a little deeper.”
“People should frame second dates as information-gathering opportunities,” says Jess Carbino, PhD, dating and relationship expert. “Do you like this person? Do you think you’re compatible? Is this someone you want to spend more time with? Do you have the same values? Those are questions you should be asking yourself on a second date.”
Meet the experts:
Marisa T. Cohen, PhD, LMFT is a relationship scientist with the Hily app.
Jess Carbino, PhD, is a dating and relationship sociologist who has worked with Tinder and Bumble.
Brenda Fahn, LMFT, is a therapist at Growing Self Therapy.
Marie Thouin, PhD, is a mindful dating and relationship coach based in California.
When devising a second date plan, the goal should be something fun, of course, but also an activity that moves this getting-to-know-you process forward. That could include anything from an adventurous undertaking neither of you have tried before to something as chill as ordering food and binging a new series.
An important disclaimer: if you decide to have someone over to your home or go to theirs on date number two, make sure you feel safe. Hosting someone on a second date is generally a better idea if you already know them through mutual friends or from a prior social setting. “Don’t do anything that you’re not comfortable with and don’t give in to pressure. Do what’s good for you,” Cohen advises.
Depending on what kind of second date suits your taste and comfort level, there are tons of creative possibilities to further clue you in about the other person. Women’s Health asked four dating experts for their top recommendations.
1. Go out to dinner.
This one’s a no-brainer, but dinner encourages more in-depth conversation than you may have had on date number one. “People tend to keep first dates short because you don’t know how long you want to be stuck there. At dinner, you can pick up a lot about the other person based on their interactions,” says Carbino.
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For example: Are they paying attention to you? How are their table manners, their eating styles? Do they want to share food? How do they interact with staff? How do they reconcile the bill? “Those are all learning opportunities,” Carbino explains.
2. Go to a comedy show.
Laughter is a key part of a relationship. A comedy show can indicate if you have similar senses of humor. “If you’re crying laughing at something and the other person is poker-faced, you may not have a connection or find the same things playful. You’ll also see how this person relaxes, has fun, and maybe doesn’t take themselves so seriously,” says Brenda Fahn, LMFT, a therapist with Growing Self Therapy.
3. Browse a bookstore.
Do you have a favorite indie bookstore, or is there a used bookshop you’ve been meaning to visit? Try taking your date there—bonus points if it has a cafe, or another place to sit down and chat. You’ll get to know someone on a whole new level as you see which books and genres catch their eye. “Seeing which sections you veer towards lets you learn what in the world you’re each curious about,” says Marie Thouin, PhD, mindful dating and relationship coach. Thouin even ended up marrying the person she had a bookstore date with early on.
4. Listen to live music.
And no, not at a loud concert where it’s hard to hear each other, stresses Cohen. But take your date to a smaller venue, like a lounge or beer garden where you can talk, sip, and enjoy tunes more intimately. “It offers great ambience and the potential to learn something about your partner if you have different music tastes,” says Cohen.“You can turn each other on to music you’re interested in and get to know each other that way.”
5. Take in a lecture.
Is the other person able to quiet down and think deeply? A good indicator of this is finding a lecture on a topic you both find interesting, suggests Fahn. It also paves the way for a meal or drink afterwards to share your thoughts and takeaways. Maybe they open your mind to an outlook you hadn’t considered, which can be an attractive quality.
6. Test your palates at a wine tasting.
If you both appreciate good vino, find a local wine tasting event. It’s elegant, elevated, and allows you to interact with each other while comparing notes. “You get to seeing how a person interacts functionally, sensorily, and kind of sensually,” says Thouin.
Pro tip: sip slowly, and make sure you’ve eaten first. The last thing you want is to get over-inebriated in front of a potential new boo.
7. Team up for an escape room.
Winning an escape room requires collaboration. Is the other person taking your ideas into consideration, or are they being selfish and ego-driven? It’s a great indicator of how you’ll work together. “Games bring out a lot,” says Fahn. “What comes out with this person, what do they do when things aren’t going their way? Can they have fun, or do they have a hard time regulating their emotions?”
8. Hit up game night.
Find a local bar on trivia or game night, and learn all about each other’s random tidbits of knowledge (or their dexterity as they extract the ankle bone in Operation). Everyone has stories behind their favorite board games, too, notes Carbino, which gives you an opening to chat about your childhoods and things you liked to do as kids.
9. Shop for groceries to cook a meal.
Once again, opt for a date at one of your homes only if you feel comfortable and familiar enough with the other person. If you do, choosing a recipe to shop for and cook is interactive, collaborative, and looser than dining in a restaurant setting. If you’d prefer to keep the location neutral, shop for ready-made items you can bring to an outdoor picnic instead.
10. Take each other apple picking.
“I’m a fan of seasonal activities. Something like apple picking is a mini-trip without the commitment of a weekend away, for example,” says Cohen. “Depending where you’re located, it’s a chance to spend the day together outdoors for an extended period of time.” If both of you are down for a second location, head home and try your hand at making a pie. Even if it’s messy, it will probably be delicious.
11. Visit an art galley or a museum.
“An art exhibit gives you something to talk about: the art. Ask them what kind of exhibit or museum they prefer and see what they say. Their choice can be meaningful,” explains Carbino. They might be a geek for classic oil paintings, or perhaps they’re out-of-the-box thinkers who enjoy deciphering the abstract. Even if your tastes don’t align, you can still exchange thoughtful, creative opinions.
12. Pick up some kayak paddles.
You probably don’t want to partake in a sweaty gym class on a second date, notes Fahn, but if the weather’s nice and both of you enjoy the water, kayaking requires working in sync to move forward—literally. Maybe you take a relaxed row around a pond or paddle somewhere you can disembark and talk for a while. Using protection is sexy, so make sure you’re both wearing lifejackets.
13. Hit the ice.
“Second dates can still carry anxiety. Ice-skating eases the focus off each other because you’re just concentrating standing upright, you’re focused on the experience. It’s less pressure, and it lends itself to coziness,” says Cohen. Lean on each other for support if you’re inclined and, post-skating, segue into a cuddle over a cup of hot chocolate.
14. Grab a set of bikes.
Whether you own two-wheelers or rent them, a bike ride is a relatively low-pressure activity that most people know how to do. “I’m not talking about serious cycling,” says Carbino. “I mean a leisurely ride to a cool pier or a park where you can sit, take a break, maybe have something refreshing to drink and talk.” Just wear helmets to ensure your second date doesn’t end in the emergency room.
15. Take a boardwalk stroll.
While stripping down to your swimsuit for a day at the beach might not be an ideal second date, an amble along the boardwalk still allows you to enjoy the ocean air. Indulge in cotton candy to pick off each other’s lips or stop into an arcade or bar along the way. Added bonus: you won’t walk away with sandy wet feet.
16. Look up at the stars (at a planetarium).
Take a cue from Friends’ Ross Geller who wooed Rachel in a planetarium at the beginning of their courtship. “A lot of cities have nighttime events with wine and music,” says Thouin. “It’s educational and interactive.” Not to mention, up at a dark sky with twinkling lights sets the perfect mood for a makeout sesh if you’re both feeling it.
17. Paint or make pottery together.
Clay or pottery painting is a great icebreaker, says Carbino. Who cares if it’s terrible? You’ll be able to see if the other person can enjoy not being skilled at something while still being themselves and having a good time anyway. Make each other a little memento and, if things don’t work out, you can always toss it.
18. Check out a sports match.
If one or both of you is a major sports fan and finding a partner who’s equally devoted is a priority, it might be worth going to a game or watching one together at a bar. “You want to feel as connected about as many things with the other person as possible,” says Fahn. “Do both of you get into it, or is one of you complaining the whole time? Also, what part of this person emerges when it comes to something competitive?” No one wants to date a sulky sore loser.
19. Go rock-climbing.
If you’re up for a more active challenge, rock climbing is adventurous, athletic, and encourages looking out for each other. If one or both of you is new to it, it’s also a chance to get out of your comfort zone. “A major component of a successful relationship is flexibility,” says Fahn. “That said, you don’t want to push people too far. If they don’t love the idea, suggest a less intense hike or a walk.”
20. Meet for a booze-free weekend brunch.
A daytime meal without any booze is a good idea if things got a little tipsy on the first date (hey, no judgment!). “It’s important to mix it up,” says Thouin. “Try getting to know each other during different times of day.”
Yes, a second date without the lubrication of cocktails can be daunting, but ultimately, it will help you get to know the other person more authentically. Skip the mimosas and Bloody Marys and chat over coffee and pancakes instead.
21. Spend an afternoon volunteering.
“Volunteer opportunities are great, like a park service or taking care of a public garden,” suggests Thouin, adding that if you bring up volunteering on a date, you can also get a sense of their reaction: Is giving back something they value?
“Volunteering can bring you closer together because you get a sense of, ‘Oh, wow, we can contribute to something greater,’” says Thouin.
22. Sign up for an improv class.
This is one takes guts. If one or both of you is shy or introverted, you should probably skip it. If you decide to go for it, Cohen says an improv class will ensure you won’t be distracted: “You’ll be completely focused on that in-the-moment experience and your connection to one another. It also shows you like to play, have a good time, and are up for anything.”
23. Visit a cheesy local tourist attraction.
Let’s face it, almost no one sees the sites their hometown is famous for. Why not play tourist for the day and stop by some local landmarks? “When we see things with fresh eyes, we’re more present,” says Thouin. Visiting a local attraction can be a fun, informative, and even a silly shared experience. If you think it will be a moment you’ll want to remember, have someone snap your photo together.
Freelance Writer
Beth Sobol is an NYC-based writer who covers lifestyle, relationships, entertainment, culture, and more. Her background includes print, digital, and broadcast media for local and national outlets. A chronic late bloomer, she only recently started to Wordle.