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Starting a conversation in online dating doesn’t require a perfect line. What matters more is whether the other person feels like replying is easy and enjoyable.
The best messages are simple:
They show you actually noticed something
They invite a response without pressure
They feel like a real person wrote them
Download the full PDF of the Professional Matchmaker's Guide to Dating - Issue 1
“Hey” isn’t wrong — it’s just forgettable.
A small upgrade is referencing something real from their profile, then asking a light question.
Real-world examples:
“That photo in Rome is great — what was the best part of that trip?”
“You mentioned you’re into jazz — do you have a go-to album?”
“Your dog looks like a character. What’s their name?”
Those messages work because they’re easy to answer and they show attention.
Here’s
the honest truth: people aren’t looking for a texting "robot". They’re looking for someone who feels normal to talk to. Mix that with curiousity about someone new and you have a strong connection opportunity and not one that's fake, one that's real. You find the topics that are mutual. As you read their profile, you see things that you have in common (the things that make you interested in them beyond looks) and right there is a menu of conversational topics that are totally safe and of interest to you both. Call them openers but they're still interesting to you both.
If someone sends something thoughtful and you reply two days later with “lol,” that creates distance. If you send three messages in a row before they reply, that can create pressure.
Don't think that you need to find the "Goldy Locks" zone, or the "just right" amount. Change your perspective totally. The real goal is not to “time” your replies perfectly. It’s to keep the back-and-forth feeling balanced. When you're comfortable and at ease and interested in the topic that the other is, then you're golden. That's what sparks that light in the eyes and the ease of conversation, and jokes...and laughter and mutual appreciation are really strong builders of attraction!
It's even backed up by science. Research supports the idea that people respond well to shared interests and the pace of engagment.
“People tend to like others who express a similar level of liking and engagement.” — Journal of Personality and Social Psychology
Source: https://psycnet.apa.org/record/1968-09328-001
OK, here is the big "give away"... the magic reveal of the Magician's trick! You don’t need to fake anything. Just pay attention to the flow and keep it mutual.
Most people try to be interesting. The better move is to be interested!
Let's start the Date-Hacking... Hack #1...A simple follow-up question makes conversations feel natural and makes people feel seen, heard, and appreciated.
Harvard U. research found that asking more questions — especially follow-up questions — increases likability.
“People who ask more questions, particularly follow-up questions, are better liked by their conversation partners.” — Harvard Business School Working Knowledge
Source: https://www.library.hbs.edu/working-knowledge/asking-questions-can-get-you-a-better-job-or-a-second-date
Real-world examples:
“That’s cool — what got you into it?”
“What inspired you to choose that career?”
“That' sounds like a good ptential. What’s something you’re looking forward to if you get it?”
It’s simple, but it’s powerful. And it's beneficial to both of you in a real way. This is the key to it all; be real and focus on the things that you have in common while learning the things you don't and seeing how you handle those things you don't. Trust builds at its own pace so you just keep telling yourself, like Roman Emperor Marcus Aurelius who had a page follow him and whisper in his ear "you are just a Man, Sir, you are just a Man"; I can feel releif in knowing that we are just ourselves and we're looking for another who is just their-self, and I'm looking for the one who is looking for me!
Online dating can feel mentally tiring (exhausting!) because there are so many options and so many micro-decisions (and tons of doubts, questions and worries).
The easiest way to stand out is to make it feel easier, not harder.
The APA has covered the idea that too much choice can make decisions more difficult and less satisfying.
“Too much choice can actually lead people to take less positive risks… and to use simplifying strategies.” — American Psychological Association (Monitor on Psychology)
Source: https://www.apa.org/monitor/jun04/toomany
So keep messages light, easy, and human. When messaging feels like work, people check out. And, really, are you being yourself? The same self that they're gonna eventually get to know? That's why being yourself upfront will lead to a much better chance of success and a much clearer and quicker idea of whether or not you're a good match (which is great for you to know and it may just end up a fun date or an amazing evening!). But, of course, not spilling everything about your life right away (taking the time building your confidence in the them), and stay at a cool, easy pace that is comfortably set by the conversation and interest itself. When you're focus is on the conversation and the fun things about it, the click starts spinning and time flies. Enjoy your date.
Reference something specific
Instead of a vague opener, mention something real you noticed.
Example:
“You mentioned you’re into hiking — any favorite spots lately?”
It feels casual. It shows attention. It doesn’t feel rehearsed.
Ask one light question
Keep it simple and easy to answer.
Example:
“That concert photo looked fun — was it as good as it looked?”
One question. Easy reply. Natural flow.
Keep it short and warm
You don’t need a paragraph.
Example:
“That made me smile. You seem easy to talk to.”
It’s friendly. It’s human. It leaves room.
Follow their lead on tone
If they’re light, stay light. If they’re thoughtful, slow it down.
Example:
If they say: “I’m a big reader.”
You say: “Same here — anything you’ve read lately that stuck with you?”
Not dramatic. Just in sync.
Sending a generic opener
Not great:
“Hey.”
Better:
“Your dog looks like a character — what’s their name?”
Small effort. Big difference.
Writing a paragraph right away
Not great:
“So I’m originally from Chicago but moved for work and I travel a lot and I…”
Better:
“I’ve been bouncing between cities for work lately — where are you based?”
Short. Conversational. Easy to respond to.
Turning it into an interview
Not great:
“What do you do? Where are you from? What are you looking for?”
Better:
“What’s something you’ve been enjoying lately?”
It opens the door without grilling someone.
Trying to be overly impressive
Not great:
“I run three companies and just got back from Monaco.”
Better:
“Work keeps me busy, but I try to make time for good food and good company.”
Let them discover you. You don’t need to announce it.
This version feels like someone who:
Has nothing to prove
Isn’t overthinking
Is comfortable
Is interested
That’s EXACTLY the energy you want!
What should I say first?
Start with something real from their profile. One small observation and one easy question is enough.
Should I ask a question in the first message?
Yes — but just one. Make it easy to answer, not something that requires a paragraph.
How long should we message before meeting?
Long enough to feel comfortable. Short enough that you’re not building a whole relationship over text.
Is humor important?
Light humor is great. Just don’t force it. Warm beats witty every time.
What if they give short replies?
Mirror the effort. If it stays short, that’s information — not something you need to fix.
How do I keep the conversation going?
Stay curious about what they share. Follow their thread instead of jumping to a new topic.
Is it okay to move toward a date quickly?
If the energy feels mutual, yes. Clarity is more attractive than hovering.
Should I double text?
If it’s to add something natural, fine. If it’s to manage anxiety, pause.
What if I’m not sure they’re interested?
Keep your tone steady and direct. If interest is there, it will show up.
How do I know if I’m overthinking it?
If you’re rewriting messages three times, you probably are. Send the kind, clear version and move on.
And remember this... the chances are.. .they're doing most, all or more of the things you're doing and thinking the things you're thinking and feeling the anxieties and doubts you are. So, help you help them help you by just being relaxed, interested, and enjoy it!
You don’t need to be perfect. You just need to be easy to talk to, interested, and engage with them. Talk about the things that interest you bot, get to know them, ask questions and always remember, the more relaxed you are, the more they are. This goes both ways... when you see them relax, you can even more.
When your messages feel warm, balanced, and curious, you’ll stand out naturally — and you’ll attract people who actually want to engage.
“Globally renowned for their work on Bravo TV’s “Millionaire Matchmaker,” the dynamic matchmaking duo of Destin Pfaff and Rachel Federoff have over 20 years of combined experience helping singles find love, teaching people how to navigate online dating, and advising couples through rocky patches of their relationships.
With a success rate of 95%, Love and Matchmaking is one of the nation’s foremost matchmaking services. The company offers its services nationwide to clients who are seeking personal attention and hand-selected matches”.
(Source: DatingAdvice.com)
That experience informs an approach centered on discernment, discretion, and realistic relationship outcomes rather than volume-driven matching.
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