Highly specific first date advice.
On silliness, familiarity, conversation, and environment.
Modern dating, at first, requires the suspension of disbelief.
As you greet your date at the door of a bar, you have to act like it’s perfectly normal to spend an evening with a stranger, even though it feels weird to talk about your brother and your nut allergy and your fear of getting older to someone you’ve never met. You become two people test-running each other to fill the most intimate position in your lives. The date might resemble a job interview: What do your parents do? Where are you renting an apartment? What was your college major?
I think small talk can be a powerful entry point into an interesting conversation (or a lasting relationship!), but first dates often remain at the surface level, as we ping-pong questions that we don’t care about the answers to. Our generation faces a barrier to being forthcoming and outwardly curious. Maybe it’s because we’ve grown up on the internet, where interaction is instant and cheap. It takes less courage to type out a message than to approach someone at a party.
In Hinge's 2025 Gen Z D.A.T.E. Report, they found that Gen Z daters are 29% more likely than Millennial daters to wait for the other to initiate conversations. When people do make it to the first date, only 30% of heterosexual daters and 25% of LGBTQIA+ daters feel they are asked enough questions. I’d like to argue that these are problems we can fix. On a first date, you’re already operating within a fantastical version of reality—why not have fun with it?
I asked my friends in their early 20s about what they think makes a first date good.
On silliness:
Iva thinks it’s “eye contact. Be willing to be weird and silly. Ask weird would you rather questions.’
My anonymous friend also supports being playful, fun, and silly. “I have the most fun when they’re not taking themselves seriously and me neither. I had a really fun first date where we pretended we were married with this couple sitting next to us.”
On familiarity:
Naina likes to “cultivate a conspiratorial vibe by telling them a secret (or saying something that’s not secret as if it is). I feel like it’s disarming and creates conversational intimacy quickly.”
Kyra knows that “some people need time to warm up to others, but I always look for immediate comfortability and openness—I like it when people are convicted, and I like it when people aren’t afraid to disagree. There’s nothing worse than someone who is just nodding and agreeing with everything you say. It indicates that they’re not really listening.”
Ellie likes when “something goes wrong and you laugh about it together, like if there’s a weird waiter or teacher you can talk about.”
On asking questions:
Isa thinks “showing interest with inquisitiveness is the bare minimum. Asking questions immediately makes the experience better. I can’t stand when someone will monologue nonstop and just wait for you to keep asking questions when they finish.”
Cleo wants you to ditch yes or no questions. “I think the best date question, which to me is also the best general conversation question, is something open ended that has the possibilities of seriousness and CRUCIALLY silliness. For example, say you’re at a birthday party, and you’re meeting a new person—instead of asking them about what they do for work, ask the person “How do you feel about birthdays?” So. Much. Possibility. You can talk about their relationship to aging, time, their worst and best birthdays, their ideal dream birthday (which is really just hearing someone’s favorite way to spend their time). How do they feel about surprises? Gifts? Celebrations? It’s endless.”
On environment:
Andres prioritizes location. “Somewhere that is neither too loud and bright or too dim and quiet.”
Dona Ekwalla prefers activity-based dates. “Whether that’s a cooking class, watching a sports game, or some kind of park frolicking, I think the conversation is more fruitful and flowing when you’re surrounded by story material. An activity makes it easier for you to prompt questions related to what you’re doing, and I think that leads to the most organic and mutually beneficial time.”
Jude wants you to ditch the phones. Jude: “The best first dates I’ve ever been on all shared one thing in common: the absence of phones. On these rare — but spectacular — dates, phones never touch the table. Neither of us are waiting on a check-in text, a work notification, or wondering what everyone else is up to. Now, I don’t believe phones are bad. Pulling one out to show a photo or compare Spotify playlists or see what mutuals you have can absolutely deepen a connection. That being said, there’s something tangibly different about the date when phones stay off the table entirely.”
On conversation:
Zack says “a good date happens when both people can carry their weight, and no one is dominating. It works because both parties are building off of each other. I can be very attracted to someone but if we aren’t in a rhythm with each other––and aren’t feeding off of each other’s energies––it isn’t right.”
William loves “banter where people get really excited to talk about something, like a very niche shared interest that we can get down into the nitty gritty about. I remember talking to someone about my favorite movie Spy, and it was also theirs. It was just exciting to talk about the plot twists and what makes it a great movie.”
Finally, I’d like to leave you with some practical advice.
Think about what your reaction would be if someone approached you. Flattered? Excited!? Now switch the roles to make yourself the initiator. You have the capacity to change someone’s day, isn’t that kind of incredible?
Set goals for yourself. If you’re at a party, start conversations with three people you think are interesting. If you’re at a cafe, talk to the person sitting next to you. Reward yourself for your courage.
Listen actively and stop overthinking. Instead of entering a conversation with pre-planned questions, pay attention to what the other person is saying, and let your natural curiosity guide you to your next question. It’s also okay (maybe even better!) to respond with your own thoughts, opinions, or experiences. Conversations shouldn’t feel like interviews; the best ones are free-flowing and take many different shapes over the course of a single encounter.
Practice, practice, practice. Conversation is a skill that you can train over time by talking to people (in real life! not on your phone!). Very few people are born with charm! Those who seem effortlessly charismatic have honed their craft over thousands of interactions.
It’s instinctive to crave deep connection, familiarity, and safety, but every friend or partner that we feel close to now was once a stranger. Dating is a way to discover and appreciate more about others, the world around you, and even yourself. Take some risks! Talk to someone new! People are generally more open, kind, and generous than your anxious mind wants you to believe.
Thank you to Hinge for partnering with me on this essay! You can access Hinge's 2025 Gen Z D.A.T.E. Report here.
This is all such good advice!! Especially about initiating a conversation or a date and not overthinking! I think we all just need to be going for it more!