The Do's and Don'ts of Dating Site Prompts
August 21, 2025
You finally open up the dating app, and there it is—the blank box next to "What makes you unique?" You freeze. Is this the best place to share your love of New York bagels? Is it too soon to mention your three divorces and obsession with Candy Crush?
Your questions and concerns are normal, and as a love and dating coach for the last 20 years, I have helped countless wonderful women pick the best prompts and answer them in a way that gives just the right kind and amount of information. Prompts are a way to wave your own green flags and shoo away the online dating riff-raff you don't want.
Please do not blow off this opportunity to present the best of who you are while still leaving room for mystery and plenty of chances for the man to lead the way. I know it's overwhelming to dive in and write these (it IS like a job interview indeed!), but it's the way a potential mate is going to figure out if they want to get to know you more.
The major pitfalls women over 50 fall into around the prompts are half-assing it, playing it too safe, or, conversely, oversharing. These dos and don'ts should help you strike a good balance.
✅DO: Be Specific, Not Generic in Your Dating Site Prompt Answers
The most interesting conversations start with specific details. Instead of saying you love to travel, say, “I once took a solo trip to Lisbon to find the world’s best custard tart.” This gives someone something to connect with—and maybe even tease you about. Specificity signals that you are a real person with a real life, and it sparks curiosity and connection.
Your first prompt is the most important; think of it as inviting someone into your world with a wink. No need to oversell. If possible, tell a story. Remember college essays? We learned the cardinal rule of writing to impress: show, don't tell, that's how you get them to remember you! Here are some great examples:
Prompt: “The quickest way to my heart is…”
❌Vague: Kindness and honesty.
✅Specific: Making me a strong cup of coffee just the way I like it, sending a funny article mid-day, and knowing the difference between Pilates and yoga without rolling your eyes.
Prompt: “A perfect Sunday…”
❌Vague: Relaxing and enjoying the day.
✅Specific: Morning walk with my neighbor before it gets too hot, farmers market haul, and prepping a big salad while listening to Carole King. Bonus points if there’s a nap and a Ken Burns doc involved.
Prompt: “I’m overly competitive about…”
❌Vague: Everything!
✅Specific: Beating my sister at Wordle, guessing movie quotes from the ‘80s, and getting my daily steps in before 10 am. (No, I don’t cheat. Usually.)
❌DON’T: Trauma Dump
It’s tempting to be radically honest in the name of transparency. But prompts are not the time to vent about your past relationships, your ex’s bad behavior, or the myriad ways the world has let you down. If you wouldn’t say it at a dinner party, don’t say it in your profile.
Respect that this is an early stage of interaction. The purpose of the prompts is to charm and enchant the reader and find ways of connecting. You are looking for things you have in common and to make sure your general vibes and orientation towards the world jive. Save the deeper stuff for a real conversation in video or in person.
Mentioning a life goal or a simple pleasure is a much better conversation starter than your last heartbreak. There will be time for all that.
✅DO: Use Playful Teasing or Humor
Playful banter goes a long way. A little self-deprecating humor (“I’ve never met a Trader Joe’s snack I didn’t love”) is often a better hook than some clever quote you found online. A great prompt response shows you’re fun, self-aware, and open to joy. That’s catnip to high-value men.
A bit of banter-related humor also keeps you out of the "interview mode" zone. This is not a performance—you’re trying to engage and you want to show your sense of humor. Try including your go-to karaoke song or a controversial opinion—just enough edge to show personality. One note: If you're going to be controversial, please be playful about it. Save rants or true upset for friends and your therapist or coach.
The thing about using humor is also that you can find out more about a person without it seeming like an interrogation. You can't just directly ask a man if he's health conscious and expect a non-defensive response, but if you do the 3rd example below, you may just get your answer without a fuss!
Prompt: “My simple pleasures”
❌Dull: Reading a good book.
✅Humorous: Stretching my hamstrings without making a sound. Fresh berries. Leaving Costco with only what I came for (it’s happened once).
Prompt: “A typical Sunday”
❌Dull: Church, chores, maybe a walk.
✅ Humorous: Spin class, smoothie, then calling my daughter to ask why my Hulu isn't working. Later: soup, ‘60 Minutes,’ and a deep discussion about whether to date again or become a nun.
Prompt: “The one thing I’d love to know about you is…”
❌Dull: What are your hobbies?
✅Humorous: Have you ever snuck healthy snacks into a movie theater, or are you more of a popcorn-for-dinner type?
❌DON’T: Write for the Wrong Audience
One of the biggest mistakes I see women making when they write their prompts is that they write with a woman reader in mind. They say things that, if they were shopping for a new female best friend, would be winners! But men and women are not alike, and it's a better strategy to write with a male reader in mind. This means
1) Straight and to the point
2) Light, witty, playful
3) Mentioning things you enjoy that there's a chance he might also enjoy.
I know I am being offensive here by stereotyping, but this is based on what actual men report that they prefer. Of course, there will be exceptions to the rule, but I am trying to limit your dating fatigue and make you the most attractive you can be to the most potential suitors, so let me illustrate:
Prompt: We will get along if...
❌You’re a grown-up who takes care of your body, owns your baggage, and still thinks a long dinner with no phones is the height of luxury.
First of all, you sound like a mean mommy who has been scarred. Second of all, long dinners are the stuff of women. Men might do it in courtship, but it's usually not their jam.
Prompt: “Dating me is like…”
❌Sunday hikes, fresh lemon in everything, laughing at The Golden Girls reruns, and then deep conversations over homemade soup and dark chocolate.
I think you can see that if you are looking for a female best friend, this is spot on, but for a man, not so much.
Try something like this:
Prompt: “Dating me is like…”
❌A good laugh, a full fridge, and no interest in fixing you—but I’ll probably inspire you to take better care of yourself.
Whatever you do, don't write what you think they want to hear, and don't be overly flirtatious or sexual if you want to attract a committed relationship. Don't answer this prompt if you are looking for something serious:
“A shower thought I recently had…”
He should not be picturing you in the shower yet!
Write what the perfect match for you would find delightful. This is how you attract good matches, not just more matches.
That might mean turning off the guy who thinks your love of obscure documentaries is boring—but it will likely attract the person who thinks that's awesome. If he’s your suitable companion, your honest, playful, properly directed profile prompts will catch his eye.
✅DO: Drop In a High-Value Detail
The easiest way to stand out and give men valuable hints on how to please you, is to drop clues about what makes you light up. Think of this as the sparkle in your eye, but in written form. What makes you feel like the most interesting woman in the room?
Whether it’s your devotion to morning dance parties, your ability to name all 50 states alphabetically, or the fact that you deeply love your pet--make sure it's included. High-value details show what you value, what your life goals are, and what you enjoy. You want to paint a picture of what it would be like to live with you and love you. Shine a light on what's special about you as if it's an afterthought.
One weird thing about me is that I remember everyone I've ever met, and if I am leading a workshop to 40 people, I learn everyone's name, but I also need to be alone for at least an hour a day, and I prefer a lot more than that. I am a 50/50 introvert/extrovert. So many of the dating site prompts will give you an opportunity to share quirky but interesting things about you that serve as conversation starters, as well as signaling the right matches about who you really are.
❌DON’T: Leave It Blank (or Phone It In)
We know—you’re busy. Or shy. Or you think your photos should do the talking. But if you skip the prompts or half-ass them, you are missing the chance to show you are a real, unique person and dog whistle at what you're looking for.
One-word answers will not do.
A prompt that says “Sundays: coffee” or “My simple pleasure: naps” doesn’t inspire a message. It doesn’t tell anyone what it’s like to be with you. It’s the equivalent of shrugging during a conversation. If you want to find a potential partner, you’ve got to give them something to work with.
You don’t need to write an essay. But answering the dating prompts with care is the best way to show effort, which is rare and appreciated. If you put time, effort, and creativity into it, it's great way to stand out.
Do you just wish online dating were easier? Maybe it would be if you had the right strategy and tools.
Go to lauriegerber.com/webinar to learn the 3 Secrets to Finding and Maintaining Healthy Love I teach all my clients, for free!
Love,
Frequently Asked Questions About Dating Site Prompts
What makes a great dating app prompt answer?
A great prompt is specific, lighthearted, and gives a glimpse of your personality. It’s more than just facts—it’s a little story or playful tease that invites someone to start a conversation.
How do I avoid waving a red flag in my prompt answers?
Avoid sharing too much too soon about past relationships or personal struggles. Keep things positive and forward-looking to signal emotional readiness, not baggage.
Should I answer all the prompts?
Go as far as the app or site allows you to go. The more you can share about yourself, the better the app will be at ruling out people who are not a good match for you. Remember, there are millions of singles near you, and you want to attract the right ones. Filling everything out shows you're serious and gives plenty of information for good matches to respond to. That said, no particular answer should be more than a few sentences; people don't read!
Are funny answers better than serious ones?
Humor is a huge plus—especially if it’s playful or self-deprecating. It shows you don’t take yourself too seriously and can make the first interaction feel relaxed.
Should I customize my prompts for different dating apps?
Yes! Each app has its own vibe and audience. For example, Hinge profile prompts are designed to spark meaningful conversation, while others might be more casual. Tailor your answers to the tone of the app and the kind of relationship you want.