Turn Your Dating App Match Into an Actual Date: Messaging Tips That Work
Introduction
You've spent some time building an attractive dating profile. While that's a significant first step, your ultimate goal is to find great candidates and turn them into actual dates in real life. You are a busy professional leading a full life. You haven’t got much time for messaging people on the apps.
So, how do you craft compelling messages that get positive responses and quickly those turn those exchanges into real life dates? Below, I’ll share my tips based on what’s worked for me.
How to improve the response rate to your dating messages
Here are some tips for making an excellent first impression on a dating app with your very first message to improve the odds of getting a positive response:
1. Start with a question
Ask a question about something in they’ve mentioned their profile, such as their hobbies, interests, and passions in life. Look through their profile carefully for clues on activities they like to do, hobbies and passions.
Good conversation starter questions to ask strangers:
Ask about any hobbies/interests they’ve mentioned on their profile. Even better if you ask them about a hobby you haven’t tried but have always wanted to try.
Questions like "What’s one of your favorite your hobbies?" or "What do you like to do to relax after a busy week?" work well because they are open-ended and give the person an opportunity to share about themselves (which most people love to do).
Ask for a recommendation on a subject they’re likely knowledgeable about. For instance, if you noticed them saying they enjoy spending time in a certain part of the city, you might ask, "I’ve been meaning to explore this [name of the part of the city]. Do you have any recommendations for good restaurants there?". If they posted that they’re an avid reader, you may ask, "I am looking for books to read about philosophy and pretty new to the topic… do you have any favorites?"
Talk about food and drinks: Most people have go-to restaurants, coffee shops or bars in their neighborhood or city. Try asking, "What's your favorite type of food?" or "Do you have a favorite dessert place around in [neighborhood or town]?" The benefit of this question is that when someone answers it, you'll already know where you can meet them on a date.
Ask about their travel experiences or recent memorable adventures. Questions like, “Have you traveled anywhere interesting recently?” or “What’s your dream vacation?” can lead to exciting conversations and shared experiences.
Discuss mutual acquaintances or events: If you know that you have mutual friends or professional contacts in common, or attended the same school, or worked at the same place, bringing up the mutual affiliation can help break the ice.
My personal favorite is to ask them, "What's something new that you've learned recently?" Since I love learning and I prefer the company of friends and romantic partners who take interest in personal development, this question has been a helpful gauge for me.
By the way, if you’re looking for more conversation starter ideas, you’ll find them in Cyranote, which uses AI to generate creative conversation prompts on your behalf when you’re stuck.
2. Mention something you like on their profile
Mention something that stood to you from their profile that you’d like to learn more about. Comment on things they shared about their interests rather than their physical appearance. Use this opportunity to ask them questions based on the interests they’ve already expressed. For instance, if a guy says he likes to volunteer with children, you may choose to compliment him, saying he seems like a really caring person and ask him what organization(s) he has volunteered with and how he enjoyed those experiences.
Alternatively, you can share something about yourself, such as, “I am a big fan of stand-up comedy and improv comedy. Have you ever tried doing improv before or seen any good shows?”
The key is to show that you are paying attention to this person. You are observant, thoughtful, and genuinely interested – and for those reasons, you will be good company on a date.
3. Be playful and flirty
Many people have given this advice. But how you implement the advice makes all the difference. What you view as a flirty message may be perceived as overbearing, aggressive, cringe-worthy, or uncomfortable by the recipient. So, how do you strike the right balance of being playful/flirty and respectful? Here's my advice:
Don't send any overly flirtatious/romantic messages to a complete stranger. Wait until you’ve received some signal that this person is receptive to this type of communication (e.g., usually once he or she has already met you in real-life and feels comfortable with you).
Start with light and fun topics. For instance, talk about a shared interest, a funny incident from your day, or something you found amusing that others are likely to find entertaining too.
Give a genuine compliment. Focus on complimenting someone's personality, choices, or achievements rather than just physical appearance.
Use humor thoughtfully. A bit of humor goes a long way in making the conversation enjoyable. However, it's essential to avoid subjects that may be offensive or too personal (e.g., about politics, religion, sex, and money).
Use Emojis and GIFs. These can add a playful element to your texts and help convey tone, which can sometimes get lost in text form. Just use them sparingly.
4. Be honest and express vulnerability
If you're new to online dating or recently got back to it after a long hiatus, you may be nervous or skeptical about the experience. Try saying, "I'm new to this dating scene, and honestly, it scares me."
To that point, being yourself is the best strategy for attracting someone compatible with you and accepting you for you. If you're a jokester in real life, joke around with the other person. If you are a serious type, it's okay to be more sincere and straightforward with your communications.
5. Leave some mystery
Don’t reveal everything about yourself at once. Save some topics for in-depth conversations later.
6. Being brief is being kind
Keep your message short and sweet, around 100 words. Being concise isn't just good for maintaining some mystery. It's a way to show that you're an effective communicator who values other people's time. Online daters are busy; no one wants to read a novel. If you send someone a freakin' novel, they may easily assume, "This individual will talk way too much in person and not give me the space to share. Hard pass!".
Tips for making a text conversation flow
The most important tip is to pay close attention to how they respond to your message. If they are engaging with your question/something you just shared, you can continue in that vein. If they are uncomfortable with your flirting attempt or conversation approach, don’t dwell on this or beat yourself up. Simplify shift your approach and try a new topic.
When is the right time to ask for a date IRL?
One of the biggest mistakes I’ve seen people make is that they spend far too long texting back and forth. They fail to capitalize on the initial rapport and use that to ask for a date. With this passive approach, one or both parties eventually lose interest in the relationship (or one person just ghosts the other). What a waste of time!
Once you've had a few turns of conversation on the app itself (5-10 messages per side at most), it is time to schedule a face-to-face date. I challenge you to try to get a date in the same session/day you sent your initial message. This direct approach is the best strategy for a few reasons.
First, you are looking for someone you can fall in love with, not a texting/email buddy. You can't assess whether you have chemistry with someone through messaging alone – you need an in-person experience with them (e.g., get a kiss).
Second, half of the battle is already won if you’ve gotten someone to respond to your intro message. When you've received a thoughtful reply to your intro message, this individual has already checked out your profile and decided that you are worth their time. In the professional realm, the analogy is that you've submitted your resume to apply for a job, and the recruiter has reached out to schedule a screening interview. The recruiter has reached out because they think you are qualified (or more than competent) for the job. You can now focus on making a strong, differentiated impression with the recruiter in a conversation.
Further, 5 to 10 turns of text conversation provides more than enough room to establish a baseline rapport with anyone; it is enough for most people to feel comfortable meeting you face-to-face in a public, neutral place. Anyone serious about dating will prefer to move the conversation into real life quickly after forming a decent digital connection with a dating candidate.
Your time is your most valuable asset, so why waste it on people who are not as serious about dating as you are?
When you ask someone for a date, be sure to propose a few specific times and meeting locations/activity options based on your knowledge and inference of what both of you would enjoy. Your goal is to get the person on the other side to definitively say "yes" or "no" rather than allowing them to stay in the terrible ambiguity zone ("Sure, maybe, let me think about it…").
Summary of Tips on Finding Greater Success with Online Dating
To improve the response rate to your messages, pay close attention to what someone's posted on their profile. Ask open-ended questions to learn more about that person; a safe starting point is to ask more about their interests/lobbies and get recommendations.
Stay attuned to how someone is responding to you to keep a text (and real-life) conversation flowing. Are they engaged? Are the text responses coming rapidly? If you sense a lull or discomfort, try a different approach and steer the conversation to another topic.
Ask someone out as soon as you've built a bit of rapport through your text messages. Do not wait and wait. The longer you wait to make the next move, the more likely one thing or another will get in the way of the two of you meeting in real life. Value your own time and respect the other person's time.
How Cyranote Improves Dating Success
Text communications are an important element of any dating relationship, and people who are newly dating tend to be the harshest judges of the text messages they receive.
Cyranote is a mobile app that helps people easily maintain fun, flowing text conversations with their dates and potential romantic partners (though we help in all types of relationships and communications). One of the app's main goals is to support people in building deeper connections with their dates in those early phases of dating. The app uses AI to understand your message threads and generates effective replies and conversation starters on your behalf.
The app will soon be available for private beta. You can join our waitlist if you are interested in trying it out.