11 Easy Ways to Start a Conversation on OkCupid - wikiHow

Tips for sending the first message on OkCupid

Written by Julianne Cantarella | Edited by Christopher M. Osborne, PhD

Last Updated: May 30, 2024

Using OkCupid is a simple and fun way to meet new people, but sending that first message to someone can be nerve-wracking. To help ease your worries, this article lists a bunch of helpful strategies that can improve your odds of OkCupid success. So read on before tapping out your next first message!

This article is based on an interview with our professional dating coach and licensed social worker, Julianne Cantarella. Check out the full interview here.

Things You Should Know

To get a conversation started on OkCupid, ask the other person things that require a longer response or refer to something in their profile.
You can also point out similarities if you have any!
Remember to keep it simple.

1

Ask a question that encourages a real response.

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Give them an invitation to share something about themselves. It’s easy to ignore messages on OkCupid that don’t interest you, so you have to give the other person a reason to get into the conversation. People are often more inclined to answer questions, especially when it gives them a reason to talk about themselves. Your entire message doesn’t need to be a question, but consider adding a question element to it to increase your odds of getting a reply.
- Not all questions are created equal, however. Try to avoid questions that can be answered with “yes” or “no” or another single word. Compare these examples:
  - “Looks like you’re quite the baker. Do you make cupcakes?” (They can just reply “yes” or “no” here.)
  - “Impressive baking skills! What’s your secret for making those giant cinnamon rolls?” (They’re more likely to give a descriptive answer here.)

2

Write about something from your profile.

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Start the conversation on familiar ground. The other person will have expectations about you based on your profile, leading them to feel like they already “know” you to a certain degree. It will be jarring to them if you send a message that is completely out of character based on your profile. Instead, confirm that the individual they know from your profile is the same person they’re getting in conversation.^{[1]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.}
- If your profile shows that you’re really into sports, you might try something like this: “Can you believe how the game ended last night? Would you have called that hit a penalty?”
- However, if you’re not really that into sports, don’t try to pretend you are because you think that will get a better response. Remember to be yourself!

3

Comment on something in their profile.

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Show them that you’ve done your “homework” and have real interest. It’s easy for the other person to ignore generic “hey there” OkCupid messages, especially if they’re getting bombarded with them. On the other hand, a message that proves you took a good look at their profile is less likely to be ignored. To really grab their attention, very specifically name something important in their profile that you find interesting.^{[2]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.}
- For instance, their profile might show that they’re really into scuba diving. You might find that fascinating even if you’ve never tried it—if so, let them know: “Awesome scuba pics. Never tried it but would love to. How’d you get started?”

4

Highlight a shared interest from your profiles.

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Make it immediately clear that you have something in common. There have to be at least a few common interests there, so browse through their profile, compare it to yours, and pick out something fun you share. Spell it out in clear language—use the actual term, like “baking,” “skydiving,” “cats,” etc.—to grab their attention.^{[3]
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- For example: “I noticed you collect classic vinyl too. I like searching flea markets for records. You?”
- Or: “We Detroit Lions fans gotta stick together. What’s your favorite Thanksgiving game memory?”
- Reader Poll: We asked 326 wikiHow readers, and 59% agreed that bonding over a common interest is a great way to start a conversation with someone online. [Take Poll]

5

Showcase your personality by being funny.

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Humor lowers the pressure and helps put the other person at ease. Most people prefer someone who has a good sense of humor, so go ahead and show it right from the start!^{[4]
X
Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.} You don’t have to come up with the world’s greatest joke—in fact, a lame joke might really work if it fits your personality and your profile. Here are a few examples:
- A pun based on their name: “Anna-body interested in chatting about kayaking?”
- A humorous observation: “Your cat looks super chill. Mine is bonkers 24-7. Does yours offer lessons?”
- An intentionally-ruined joke: “Knock-knock. I’m here. Realizing this was a terrible way to start a conversation.”

6

Admit that you feel a little awkward or nervous.

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It’s okay to be self-effacing instead of overly confident. Striking up a conversation with a stranger who you only know through their profile doesn’t come naturally for most people. Instead of trying to mask your feelings of awkwardness with false bravado, lean into it and let it show in your message. Your greeting will feel more genuine and true to who you are.
- Using words like “sorry,” “probably,” “kinda,” “apologize,” and “awkward” actually increases your odds of getting a reply, according to OkCupid’s research—especially if you’re a guy.^{[5]
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- Adding a light-hearted touch to your message can really raise the other person’s comfort level.^{[6]
  X
  Expert Source
  
  Julianne Cantarella
  Dating & Relationship Coach
  
  Expert Interview. 6 August 2021.}

7

Give a sincere and polite compliment.

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Use “cool” and “fun,” not “hot” and “sexy,” in your compliments. It’s easy to go from complimentary to creepy when you comment on someone’s looks based on their profile pics.^{[7]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.} According to OkCupid’s internal research, words like “hot,” “sexy,” and even “beautiful” don’t work well because they’re superficial and aggressive. It’s far better to stick to compliments that lack objectifying or sexual overtones.^{[8]
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- If you want to comment on how great they look in a profile photo, try something like this: “What an awesome profile pic with that fun blue dress. What beach was that?”

8

Type out what you’d say in person.

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Don’t overthink things—be friendly and a little flirty. Ask yourself how you’d strike up a conversation with this person face-to-face, then translate that strategy to OkCupid. The phrasing and focus might end up a little different, but your tone should be very similar—fun and a bit flirtatious!^{[9]
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Expert Source

Julianne Cantarella
Dating & Relationship Coach

Expert Interview. 6 August 2021.}
- For example, be honest that you’re not a Monday person, but put a little positive spin on it—instead of starting your comment with “I hate Mondays,” try “I love when Monday’s over with.”
- Or, try to be flirty, funny, and self-effacing all at once: “Fancy meeting you here...or there...yikes I’m bad at this.”
- Here’s how OKCupid sums up the ideal strategy: “Date like you do in real life.”

9

Keep it simple with a pleasant greeting.

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But show more effort than just tapping out “hey.” A short, simple greeting can get results, but only if you put some thought into it. Skip generic options like “hey,” “hi,” “hello,” or “holla” at all costs. Instead, either use a question-as-greeting that invites an answer (like “what’s up” or “how’s it going”) or an off-the-beaten-path greeting (like “howdy”).^{[10]
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- Add the person’s name or something else unique to the greeting to help it stand out: “What’s up, Wayne from Westwood?” or “Howdy, Hannah.”
- One- or two-word greetings, especially when they aren’t specifically relevant to the other person, indicate to them that you’re not really interested in making a genuine effort at connecting.^{[11]
  X
  Expert Source
  
  Julianne Cantarella
  Dating & Relationship Coach
  
  Expert Interview. 6 August 2021.}

10

Show off your writing skills (a little).

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Use full words and sentences, not “ur,” “ya,” “luv,” etc. No, your conversation-starter doesn’t need to be super formal and perfectly grammatical. But it also shouldn’t read like a quick text you sent off to a friend. Filling your message with abbreviations and clipped phrases indicates a lack of time and effort, while a better-written message indicates interest and thoughtfulness. Compare the following:^{[12]
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- “wat up luv ur lax pic hit me up k”
- “Awesome lacrosse pic. Do you ever go to the pickup games at West Park?”

11

Write a message that’s not too short or too long.

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OkCupid’s research says 40-90 characters is the ideal length. Think of yourself as Goldilocks aiming for the “just right” size—not too short, which indicates a lack of effort, and not too long, which can seem boring or intimidating. Finding that “sweet spot” in between means you need to get to your point fairly quickly, but also leaves you enough room for some fun and creativity. Compare the following:
- “Cool mountain bike. I have one too. What’s your favorite trail to ride?” (good length)
- “Hey, I like mountain biking too.” (too short)
- “That’s a killer Yeti cycle in your pic. I have a Trek but am thinking of trying something new. What do you think is the best mountain bike?” (too long)

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Tips

Not sure how to send that first message? Here’s how you do it:
- “Like” them by dragging their photo to the right or clicking the heart icon in “Discover,” or by visiting their profile in “Questions” and tapping the “Like” button.
- Once you’ve “Liked” the person, click the “Message” button that appears on their profile. Type and send your message—but remember that you only get one shot!
- Wait for them to (hopefully) “Like” you back and respond, at which point you can continue the conversation. Otherwise, try again with another potential match.
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