What to talk about on a first date when you haven't dated in 20 years

If you haven't been on a first date since the '90s, the conversation probably worries you more than the outfit. What if it goes quiet? What if you talk about your ex for twenty minutes? What if you've simply forgotten how this works?

Here's the good news. You don't need clever lines or a store of fascinating stories. The people who do well on first dates ask easy, open questions, listen to the answers, and then ask a second question about what they just heard. Share a little of yourself in return, keep the past to a sentence or two, and most of the conversation takes care of itself.

That second question matters more than it sounds. Researchers at Harvard studied face-to-face speed-dating conversations and found that people who asked more follow-up questions were more likely to get a yes to a second date (Huang and colleagues, 2017). Showing someone you heard them is most of what being good company means.

Below are questions that open people up, what to say (briefly) about an ex, your kids or a spouse who died, and what to do when it stalls.

Why questions beat good stories

When you're nervous, the instinct is to fill the air. You tell the one about getting lost in Lisbon, then the one about your job, and then you notice you haven't asked them a thing in ten minutes.

Most people would rather be asked. In a 2025 survey of about 30,000 Hinge users worldwide, run by the dating app itself, 85% of daters said they're more likely to want a second date when they're asked thoughtful questions (Hinge). The same report found that only 30% of straight Gen Z daters (ages 18 to 28) feel their dates ask enough questions (Hinge). That second figure comes from a much younger crowd, but nobody outgrows liking to be asked about themselves.

The kind of question matters. "What do you do?" and "Where did you grow up?" are fine, and you'll probably ask them, but they lead to short, factual answers and a whiff of job interview. Better questions ask what someone enjoys, looks forward to or cares about. People light up when they talk about those things, and you learn far more about them.

Questions that open people up

You don't need all of these. Pick three or four that sound like you and let the rest go.

To get started

• What's something you're looking forward to this month?
• What's the best thing you've eaten lately?
• Have you always lived around here, or did something bring you here?
• How did you spend last weekend?

Once you're both relaxed

• What's something you've gotten into in the last few years?
• What does a really good Saturday look like for you?
• Is there a place you keep meaning to go back to?
• What's something people are often surprised to learn about you?

For a bit of fun

• What's a small thing that always improves your day?
• What were you obsessed with at 15?
• If tomorrow afternoon were suddenly free, what would you do with it?

The follow-up does the real work

Here's the whole technique: listen for one word or detail that seems to matter to them, and ask about that.

A sample of how it can go. Your date says, "I've been doing a lot of gardening since I moved." You could ask, "What are you growing?" and then, "What got you started?" Two questions in, you're hearing about their move, their new place and what they missed about the old one, and you've barely had to think.

Then give something back. Good conversation goes back and forth like a gentle rally. "I've killed every tomato plant I've ever owned, so I'm impressed" is a perfectly good return. It shows a bit of you and passes the ball back.

Notice the small moments

The relationship researcher John Gottman calls the little ways people reach for each other "bids": a comment, a joke, a smile, pointing something out. In a study that followed newlyweds for six years, couples who stayed married had turned toward each other's bids 86% of the time, while couples who divorced did so only 33% of the time (The Gottman Institute).

That research is about married couples, but the habit works from the very first evening. When your date says, "Oh, look at that dog," or "I love this song," it's a small invitation. Turning toward it ("He's very pleased with himself, isn't he?") does more for the evening than any polished line. Missing it because you're busy planning your next question is an easy mistake when you're nervous, so give yourself permission to drop the plan and just respond.

What to say about an ex, your kids or a late spouse

All three will probably come up, often in the first half hour. The rule is the same for each: say a little, say it truthfully, then come back to the present. Two or three calm sentences is plenty. The full story can wait until there's a relationship to tell it in.

Your ex

Keep it short and neutral, and skip the blame even if it's deserved. People listen less to the details than to how you sound, and bitterness tends to worry them.

You could say: "I was married most of my adult life, and we split up two years ago. It was the right call for both of us." If they ask what happened, a sample answer is: "We wanted different things by the end. It took a while, but we've both landed on our feet." Then ask them something.

Your kids

Talk about your kids the way you would with a new friend, with warmth and without the full biography. Their ages, one thing you love about them and roughly how your week works is enough. A line like "I've got two teenagers, so my life is mostly driving and groceries, and I love it" tells your date a lot in one breath.

One photo, if they ask, is lovely. Twenty is a slideshow.

Save the bigger questions, like how they feel about dating a parent or when you'd ever introduce someone, for later. Our guide to when to introduce someone to your kids covers that part.

A spouse who died

If you're widowed, you may worry that mentioning your husband or wife will cast a shadow over the evening. Said simply, it rarely does.

You could say: "I was married for 30 years. My wife died three years ago. I still miss her, and I'm also ready to meet someone." Saying both halves helps. Your date hears that the love was real and that you're here for the right reasons.

It's fine if your voice catches. "Sorry, it still sneaks up on me," and a sip of water, is all that's needed. If grief still floors you most days, a grief counselor can help, and there's no deadline for dating. Our guide to dating after losing your spouse talks about timing.

If your date is the one who's widowed, the kindest response is simple: "I'm so sorry." Then follow their lead. Some people like to share a memory. Others would rather move on, and that's fine too.

Topics to save for later

Nothing is off limits, and you'll get a feel for the person in front of you. Still, a few subjects usually go better on a third date than a first. Detailed money talk (salaries, settlements, debts) can wait. So can full medical histories, the legal side of a divorce or custody arrangement, and a rundown of everyone you've dated since. Values are fair game, so it's fine to say your faith or your community matters to you. Arguing about last night's news is a lot for the first hour.

If the conversation stalls

Every conversation has quiet patches, including great ones. A pause of four seconds feels endless to you and perfectly normal to them. When you want to restart, try one of these.

Go back to something they said. "You mentioned you're visiting your sister next month. Where does she live?" This is the follow-up habit again, and it works even an hour later.

Use what's around you. The menu, the music, a painting on the wall, the couple at the next table having a lovely time.

Name it, lightly. "I'm a bit out of practice at this, so forgive me if I ask something odd." Most people relax when you admit you're nervous, because they are too.

Showing interest without performing

Being interested beats being impressive, and it's much less work. Put your phone face down or in your bag. Use their name once or twice. Remember the small things: if they mention a dog called Biscuit, ask after Biscuit later. Laugh when something's funny, and don't force it when it isn't.

Keep a rough balance, too. If you notice you've been talking for a while, pass it back: "Anyway, enough about my garden. How about you?"

A five-minute warm-up before you go

Before you leave the house, take five minutes with this checklist:

1. Three things from your own life you'd enjoy talking about. A trip, a hobby, something funny from this week.
2. Three questions from the list above. Write them in your phone if it helps.
3. Your one- or two-sentence line about the past. Your ex, your kids or your late spouse. Say it out loud once in the car so it comes out calmly.

If you haven't settled on where to meet yet, our guide to first-date spots after 40 picks places quiet enough to hear each other.