Online dating can be tricky because you don’t get to meet the person immediately. However, effective conversation starters can help break the ice and get the romantic fires burning. Use these 20 online dating conversation starters to make your messages unforgettable.
If you’re using online dating conversation starters like “Sup” or “Hey Sexy,” you’re doing it wrong. The chances of you sparking any kind of connection are slim to none. Their mailbox is probably full of messages like that, so your generic introduction won’t stand out. Besides, what can the other person say to that besides something equally trite?
Whether you or they make the first move, you’ll need conversation starters that work. Otherwise, it’s game over. And no conversation means never learning whether there’s compatibility.
Poor conversation skills can also make an awkward moment even worse. Meanwhile, dating online presents unique challenges, such as being unable to meet face-to-face and missing out on critical social cues. That doesn’t stop 19% of global internet users from having or maintaining an online dating profile. It’s also not a factor for the 25% of married couples who met online.
Finding a match is about your timing, approach, presentation, and preparedness – or what I like to call your “TAPP.” Keep it cool but make it unforgettable. Here are some more ground rules for starting a conversation on an online dating site:
- Pick a site that matches your personality and lifestyle. Do you like scuba diving on the weekends with your pet iguana? There’s probably an app for that.
- Check out each person’s profile because you’d want them to do the same. Find out what you have in common and use the information as a conversation guide.
- KISS: Keep It Simple, Stupid. It’s harsh but true. Maintain a lighthearted and friendly demeanor by avoiding triggers, sensitive topics, and controversial subjects. You can dig deep later.
- Use your manners. Show some R-E-S-P-E-C-T or find out what it means to remain single. Nobody wants to date a rude person, and a sense of humor never hurts.
- Show interest with your active listening skills. Maybe you can’t lean in or make flirty eye contact, but you can ask follow-up questions to show you were paying attention.
Remember, questions can help break the ice and take the conversation to unexpected places. Ask about their hobbies, preferences, and favorite things. Or bring up something from their online dating profile. BONUS TIP: Give specific details about something that caught your attention to help boost the ego and elicit a positive response.
“The goal of starting a conversation online is to get to know each other, not to make the other person fall in love (yet).“
You’ll impress the right people if you act like yourself and have a little fun with it.
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Online dating conversation starters might seem contrived, but it’s all in the delivery. And sparking a friendly chit-chat is one thing, but keeping it going is another. To be successful, get comfortable engaging with people you just met. Practice interacting with them in fun, non-threatening, and exciting ways. Or use familiar relationships as rehearsals to get to know others on multiple levels.
Not every attempt will have identical results because you’re playing a numbers game. Reach out with one of my top 20 online dating conversation starters, and if you don’t get a response in a few days, move on. It’s anyone’s guess why they’re unresponsive, so don’t stress.
It could be that the online dating site is keeping useless profiles to make it look like they have more people signed up than they really do. Learn how to spot fake profiles before wasting your time.
Keep in mind, though, that no response isn’t an automatic indication of deception. It could be that the other person checked out your profile or profile picture and is disinterested. Who cares? You’re fantastic, and many others are waiting for a meet and greet. When you find “the one”, you won’t even remember who rejected you anyway.
“Embrace your online dating adventure as an opportunity to discover more about yourself and others.”
Use thoughtful conversation starters to get more relaxed around each other before the first date. You can give compliments but be careful. Avoid mentioning the other person’s appearance because it can make them uncomfortable. Only tell someone they’re beautiful/hot/handsome/an undiscovered supermodel after you’ve met and received the “okay” signals.
TIP: Use my 3-2-1 Online Dating Technique to get the most from your online dating experience.
My clients know online dating is a safe and effective way to meet like-minded people. They just need some help making it work perfectly for them. Dating is not a one-size-fits-all ordeal, so neither are the conversation starters that go along with it. A recent study proves that 50 million Americans agree. Those people have used or continue using online dating apps to find a love connection (or just a good conversation).
However, about 84% of dating app users report looking for a serious relationship online. This is why online dating conversation starters are essential.
Aside from being introduced through mutual friends or randomly running into each other in some made-for-TV miracle moment, online dating is likely your best bet. It’s the second most popular way to meet people nowadays, so you need to TAPP into that.
Avoid being cast as “the weirdo, “the creep”, or “the one with the corniest pick-up lines.” Get things moving in the right direction with my funny, creative conversation starters for online daters. You can spend a lifetime making the perfect online dating profile to no avail. Your efforts won’t matter if you can’t break the ice with your winning conversation skills.
We all know dating can be tricky, even if you’re not online. It’s particularly challenging for the recently single trying to re-enter the dating pool. Finding a match is only the beginning. Then comes the awkward introduction and the “get to know you” phase, given one of you initiates a chat. In a world obsessed with looks and convenience, online dating conversation starters help you stand above the cute competition to approach people with confidence.
Time is of the essence in online dating chats. You have to get people’s attention and find ways to keep it despite a hectic schedule.
“Worse, men are 25% less likely to respond after six hours.”
The likelihood of women responding drops 5% initially and then sharply declines with each passing hour. Here are 20 conversation starters to help avoid getting ghosted:
Examine their profile to look for clues about who they are and what interests them. This will give you a glimpse into what it would take to connect with them in a meaningful way. A good online dater will leave clues, hints, and statements in their written profile you can use to start a conversation.
People want to connect, or they wouldn’t be on an online dating site. Start by using your profile picture as the “hook” that helps you engage. Then create a bond by bringing up common interests or asking questions about their profile. Do they live in Tuscon, Arizona? Share a story about your visit, or find out where the secret hot spots in town are.
Everyone loves to talk about their passion; use this to your advantage. If you notice their profile picture is of them running a marathon, skydiving, or rock climbing, mention it. Say things like, “Wow, I’ve always wondered about that. How was it?” or “Running a marathon is impressive. Any tips on training for one?”
Kick things off with a simple, non-threatening, non-controversial request for their opinion. This gives them the impression you enjoy their good taste and admire their intelligence. People love to flex, so try to coordinate your request with something relevant to their profile.
This online dating conversation starter revolves around a statement and its feedback. That means using the other person’s comments as material for follow-up questions and compliments. For example, you could say, “I just updated my profile picture. I’m sort of digging it. What do you think?” or “I just joined XYZ. What was your first impression?”
This conversation starter is based on a technique made famous by Benjamin Franklin. It’s also inspired by cognitive dissonance, a state of mind that causes contradictory thoughts about a single topic. Here’s how it works:
Being asked a favor suggests a subconscious preference. If you ask a favor and someone grants it, that person is more inclined to like you back. They’ll also be more likely to engage with you and open up about personal topics. Excellent examples for online dating are, “Do you know which platform is streaming a hot new show?” or “I really admire your skills in XYZ. Care to give me Cliff’s Notes?”
This conversation starter is a double-whammy. It gives you a reason to compliment them and get to know them better. Plus, it makes you look like someone unafraid of humility.
How can you reminisce about pleasant memories with someone you’ve never met? You bring up shared, cultural, or global events instead. For instance, most people have fond memories of where they grew up. I grew up in a small Texas town, and I loved it. My life wasn’t perfect in Kerrville, but the things I remember bring back warm and fuzzy feelings. You can use something like this to your advantage, sparingly.
If they mention their hometown, it’s probably important to them. Ask about it. Discuss some of the similarities and differences between your childhood homes. Questions such as “What was it like to attend a school that size?” and “Did your community have any unique quirks like mine?” are safe places to start.
Stick to questions about the location, not the relationships. Don’t pry about family dynamics, past loves, or education. These can become negative triggers that derail the conversation and paint you as insensitive or nosy.
You probably live nearby singles if you’re using an online dating site or app. Many of your matches might even be in your area. However, that information is good for more than proximity. Use it to start a conversation about shared encounters, travels, and discoveries.
Not sure yet what you have in common? A clever conversation starter would be to ask about their experience on the dating site. You might discuss the craziest pick-up lines, funniest conversation starters, or lamest responses. This will help lighten the mood and make the situation feel less serious.
Maintain a casual but flirty vibe by mentioning your favorite local recreation activities. Make the topics generic but geographically relevant. Don’t ask about specific places they like to frequent because you might look like a potential stalker. Nobody wants to start a conversation that way.
This might sound counterintuitive, but hear me out. This clever conversation starter for online dating does easy work of discovering the other person’s pet peeves. A standard example would be, “What’s the worst date you’ve ever been on?” Suddenly, you know what NOT to do if you ever go out together.
It’s a bold opener, but it demonstrates you’re in the same boat. It’s an effective method for making the conversation feel less like a job interview and more like a chance to commiserate. Note the foods, activities, events, and behaviors they dislike to create a guide for your first date. Then gauge their reactions and responses to weed out people with unreasonable expectations, bad manners, and poor social skills.
Nostalgia provides a common thread for us to connect with others. At the same time, pop culture always trends positively. Throw out a funny comment, joke, or memory about a well-known band, TV show, movie, or personality. Or host a private “Where Are They Now” session in your online dating inbox.
“Which 90s Backstreet Boys song was your favorite?” paints you with a personality and sense of humor. “If you had to pick one of the Beatles to hang out with, who would be it and why?” makes you seem curious and open. You can also ask “whatever happened to” and “did you ever imagine” questions. Go beyond the mind-numbing “hey beautiful” texts that keep getting ignored.
Start with simple questions like “What was the last concert you saw?” and “Where is the last place you traveled?” This will open a dialogue that could go in multiple directions. Begin talking about concerts, and end up discussing your hometown experiences with the high school band.
You don’t have to be cast in a Hallmark movie to show your sensitive side. Besides, your date probably wants to know you’re a living, breathing human being, not a chatbot posing as a potential date. “I had the biggest celebrity crush in school” should elicit a humorous or thoughtful response, not an empty “Hey there” or “That’s crazy.”
Meanwhile, we all fall flat on our faces from time to time. Lasting love is built with people who can laugh at their mistakes and carry away lessons from the mayhem. Start a conversation about an embarrassing moment to gauge their self-confidence and comfort level with you. Just don’t push too hard to get them to share a mortifying story. We all deserve our privacy and dignity.
Some people view their pets as part of the family, so it makes sense to ask about them. This casual icebreaker can lead to hilarious anecdotes, warm walks down memory lane, and follow-up questions for you. It’s also a great way to find out if they have any pets you’re allergic to or whether you need to plan dates closer to home.
The best online dating conversation starters create a sense of excitement for future potential.
“Everyone has a fantasy, and asking someone about theirs will help you discover what they value in life.”
Play into it with flirty, thought-provoking questions like these:
- If money were no object and you could quit your job tomorrow, where would you go, and what would you do?
- If you could fast-forward your life one year, where would you be, and what would you be doing?
- What does your dream date look like? Describe it in as much detail as possible.
Use the information from this conversation as a guide for future romantic getaways, couple’s goal-setting, and date night planning.
What would you choose if you were stranded on a desert island and could only carry three things? Notice how you’re automatically inclined to think about and answer that question. The person on the other end of your favorite dating site will probably act the same. Not only is it an interesting question, but it’s also an effective conversation starter for online daters.
You can also get more specific by asking which three books, foods, people, or pastimes they’d take. This gives you insight into how they prioritize responsibilities and relationships and meet unique challenges.
Ask for their advice to get the conversation rolling. Most people love to feel like their opinions and skills matter. Show the person you’re talking to that you care about them. Request insights, perspectives, advice, and knowledge to demonstrate respect for their beautiful minds.
Perhaps their online profile photo references a specific hobby or interest. Weave it into your conversation starter with an attached question or request for advice. This is a lot like asking for their opinion, except it’s about their unique wisdom or skillset instead. It’s an online dating conversation starter that helps you learn about the person behind the profile.
Consider the person’s age when initiating a conversation online or on a dating site. This is important because your matches can respond differently depending on their generational influences.
People between 18 and 23 like to talk about surprising or unique topics. Pair other conversation starters with whimsical questions like “Pain reliever personality test: Tylenol, Advil, or Anvil?” Approach people 24 to 28 with lifestyle-related questions. Try inquiries like “Do you enjoy sleeping in or getting up early on the weekends?” and “Which do you prefer: skiing, scuba diving, or rock climbing?”
Looking for someone 29 to 35? Break the ice with more personal questions. A lighthearted game of “Would You Rather” might work. Anyone over 35 will respond best to pop culture questions and historical references.
Everyone likes a good joke or funny reference. However, hilarious conversation starters work best when delivered with flair. Single women are more likely to respond positively to a humorous message because females value a sense of humor in men. Trust the science.
That’s not to say men don’t also appreciate funny women. Pick a GIF to capture their attention and attach a joking comment. Not a comedian? Start with a silly knock-knock joke or tell them a funny, relatable story.
Find common ground based on their profile information. Or pick something from one of their photos and lightly tease them about it. For example, “Is that really your dog, or did you just post it to get my attention?” or “Was it necessary for you to be so interesting? Can you save some of the awesomeness for the others?” This creates intimacy and lets you see if they can take a harmless joke.
This conversation starter works exceptionally well for men because they’re generally the more straightforward sex. It’s also why men are 98% more likely to respond to an invitation or well-put-together conversation starter. However, a no-fuss icebreaker can be just as effective on some women.
Consider “Drinks soon?” or “Free this weekend?” when using dating apps like Tinder and Plenty of Fish. You already know the other person finds you attractive since they had to match you before chatting.
Talking about the future in general terms can spark the imagination and come across as flirty or witty. It’s also a terrific way to demonstrate your sense of humor about online dating. A simple question like “So, two kids or three?” can be playful but show you’re serious about a long-term relationship.
Constant messages about flings and hookups can get annoying. Stand out by jokingly referencing your plans for the relationship, not just for the night. As much as everyone appreciates compliments, the neverending “You’re hot” and “Hey sexy” doesn’t cut it.
Society frequently surprises us with groundbreaking trends and questionable fads. Fortunately, they can make terrific conversation starters for online dating. Here’s an example: “Can you believe they’re bringing the ‘80s back with those stonewash jeans from Calvin Klein?” This helps you gauge their fashion sense and determine how closely they follow the trends.
Not concerned about your date’s closet? This conversation starter can also help reveal their pop culture knowledge, educational background, emotional intelligence, and biases. It’s a clandestine way to screen potential mates before allowing yourself to discuss more personal topics. Chatting about trends also keeps the conversation fresh since there are fads in every industry.
The 2×2 conversation starter technique is simple. First, you send a message with two interesting facts about yourself plus two questions you want to know about the other person. This gives them something to ponder and something to respond to. The back and forth can continue as long as you have interesting facts and compelling questions.
This might seem like a typical Q&A session, but it’s different. The 2×2 conversation method allows both people to get to know the other based on information they’re willing to share upfront. The questions are only there to keep the dialogue going. Learn the art of conversation to make sure you don’t take things too far too fast.
Find out what foods, items, or activities the other person can’t live without. Perhaps share a few of your must-haves to get the conversation started. Mention your favorite dishes, specific possessions you never leave the house without, and everyday habits you’ll never quit. If possible, align your fascinations with their interests and values.
An example would be, “I see you enjoy Mexican food. I’d probably starve without street tacos.” Another is, “As a fellow musician, I know you’d love my collection of vinyl albums.” This sparks a conversation over shared interests, integrates trends, and inspires a more meaningful connection despite online dating restrictions.
Conversation starters can only get you so far in online dating. The reason is that people have to discern your personality by dissecting the things you say (and don’t say). This can be risky for someone unprepared. Check out these fundamental rules so your online dating conversation starters don’t turn into conversation enders:
- DON’T ask yes-or-no questions. Use open-ended questions instead because they feel more like an explanation or conversation than an interview or interrogation.
- DON’T do all the talking. Let the other person speak and avoid interrupting. Cutting off potential mates can seem rude and dismissive, even if you’ve already proved otherwise.
- DON’T reveal too much too soon. Leave something to the imagination and give a reason to come back for more. Too much of a good thing can scare another good thing away.
- DO be humble. People usually don’t respond well to those who brag and boast unprovoked. Save your success stories for appropriate exchanges where the other person can also shine.
- DO listen/read carefully. It’s okay to miss a few details here and there, but don’t appear to be ignoring the other person. Repeat what they say if that helps you remember it.
- DO keep it casual. Online dating conversation starters should be entertaining, imaginative, and flirty. Topics involving personal matters can make the other person feel invaded.
Conversation starters for dating make it easier to meet people online and form long-lasting relationships. They also help you start out casual and gradually work your way into more intimate topics based on your feelings. Using the top 20 conversation starters listed here gives my clients a fighting chance to find love and keep it.
Knowing how to start a conversation with anyone you’re interested in is a love-and-life skill. Online dating conversation starters help reveal a person’s true nature. They uncover their values, world views, hopes, dreams, expectations, goals, and everything in between.
“Most importantly, conversation starters help determine whether the person on the other end is compatible with you. Is it even worth going on a date with them?”
I remind my clients that online dating is a numbers game, and not everyone will click with you. Don’t overthink it, keep your conversation starters simple, and enjoy the other person’s company. If love is a battlefield, show up with conversation starters that make the competition moot.