Let’s start with some good news…if the matches are rolling in, your dating profile is doing its job. Your photos are working. Your bio is telling a story people want to hear more about. So let’s start by giving you some credit, friend. That’s not nothing!
I hear things like, “Amie, I’m matching… but literally I’m getting no dates! What’s wrong with my approach?”
If that sounds like you, stuck somewhere between making the match and actually landing a first date, you should listen up. The initial attraction is there, but the connection is falling flat.
And here’s the good news: that’s a skill. Skills can be learned.
So let’s walk through the seven most common reasons I see matches fizzle out before they ever turn into a date, and I’ll tell you exactly what to do instead.
1. Your Openers Are Boring
I’m just going to say it: “Hey, how are you?” is not an opener. YAWN… that is such a boring question as your introduction on an app.
Think about it from the other side. They’re getting that exact same message from 10 other people in their inbox. What’s going to make you special and stand out from the rest? Nothing.
And a message that takes zero effort usually gets zero effort back. Or no reply at all.
The Fix: Make it personal. They took the time to write a profile, so use it. Scan through their profile…choose something specific and ask about it.
- Instead of “Hey, how are you?” try: ” Wow, is that you scuba diving? Where did you go, and how long have you been diving for? “
- Or: “You said you know the best tacos in town. Bold claim. Don’t gatekeep lol, what is the best spot?”
A personal opener says, “I actually read your profile, and I’m curious about you.” That’s attractive. That gets replies.
2. You Talk at People, Not With Them
I look at so many dating conversations posted online, and this really seems to be the biggest failure: Talking without asking.
And the singles I work with tell me this is their biggest pet peeve.
You might be excited and chatty. That’s understandable. You want them to get to know you, so when they ask a question like “Tell me about your vacation in Mexico, it looks great.”
You just answer it point-blank. “It was so good! I loved the trip and the food was amazing.”
No follow-up get-to-know-you questions like, “Have you ever been to Mexico too?” Nope…just a short answer that leaves no room for a back-and-forth conversation. That’s a missed opportunity.
Conversation is a game of catch. If you keep holding the ball, the other person gets bored standing there on the sidelines.
The Fix: Ask questions to learn about them. Share a little, then toss it back.
- “I spent Sunday at the farmers’ market. I’m a sucker for fresh peaches. What does a perfect Sunday look like for you?”
- “I’m reading a great book about vampires right now. Nothing too scary and just slightly sexy. What do you like to read?”
- “I used to play tennis with my brother all the time, but he’s so busy now. I’ve been looking for a new tennis partner. Do you play?”
You share a key detail about who you are, but now they’re invited in. That’s the difference between a monologue and a connection.
3. There’s No Depth in Your Questions
Now, some of you are saying to yourself, “Amie, I do ask questions!” Okay, great. But does it feel like you’re building a connection? Or are you asking interview questions?
Do you care about the answers? Or are you just passing the time and making small talk?
- “What do you do for work?”
- “What are your favorite hobbies?”
- “Do you have family nearby?”
Yes, you are asking questions, but there is no depth to the questions. You’re not asking about them, specifically.
Or, worse, maybe you’re asking yes or no questions and slowly killing the chat.
- “Do you have plans this weekend?”
- “Are you an outdoorsy person?”
- “Do you like music?”
Maybe you’re not asking enough follow-up questions. You barely scratched the surface with one answer, and you have moved on to the next topic. It feels like an interview rather than a connection is being made.
The Fix: Stop interviewing and start getting to know their passions. When they answer, stay there and go one level deeper.
- They say they love to travel? Don’t jump to the next question. Ask, “What’s the one trip that changed you?”
- They’re a teacher? Ask, “What made you want to do that? Was there a teacher who inspired you?”
People light up when they talk about what they love. When you help them feel that spark, guess who they associate that feeling with? You.
4. You’re Making Them Your Pen Pal
Oh, the pen pal trap. Tale as old as online dating. You’ve been messaging for three or four weeks. You’ve built an emotional connection, but you don’t have plans for date.
Isn’t the whole point of online dating to meet someone in person?
Talking for weeks is a waste of both of your time. You might know their childhood pet’s name and their favorite coffee spot. But if you still haven’t made a date… then what’s the point?
I tell the singles I work with that the longer they text, the more they build up a fantasy version of each other. The worst part about that is that when you meet in person, the whole connection could fall flat.
Chemistry lives in real-time connection, not in an endless inbox chat.
The Fix: Learn how to move things forward. Here’s the rhythm I teach:
- Chat in the app for about 3 days: Your goal is to see if there’s an actual spark or some kind of conversational chemistry that’s worth your time.
- Then move it off the app: a phone call, a video chat, or texting. Hearing someone’s voice or seeing them laugh tells you more in 10 minutes than a week of messages. And it helps you really gauge chemistry.
- Three days after that, ask them out: Keep it simple and specific. “I feel like there is a connection here. Would you like to continue the conversation in person over coffee? When works for you? I’m free Thursday.”
Momentum is your friend. Don’t let a great match go stale waiting for the “perfect” moment.
5. You’re Waiting for Them to Make the Move
Okay this one, I want to make clear that there are no gender roles to asking each other out. So many singles tell me, “If they’re interested, they’ll ask me out first.” Wrong!
I’m all about taking charge of your love life. If there is a connection with someone, go ahead and be the first to ask them out.
The Fix: Just ask. It doesn’t matter who does it first. And let me tell you, confidence is sexy, and a clear invitation takes the guesswork away.
What’s the worst that can happen? Someone says NO? And now you know, and you can put your energy toward someone who will say yes.
6. Your Invitation Could Be Too Vague
Don’t just say things like… “We should hang out sometime!” or “I’d love to bring you there one day.”
This feels so noncommittal. It’s playing it safe, and there’s no forward momentum.
A vague promise sounds like wishful thinking. It doesn’t sound like an action is being taken. You need to do more than hint.
The Fix: Instead I want you to be specific. Name the what, the where, and the when.
- Vague: “We should get drinks sometime.”
- Specific: “There’s a cute wine bar on 5th I’ve been wanting to try. Are you free Wednesday around 7? If not, when will you be free?”
A specific invite shows intention. It tells them you’re serious about meeting, and it makes saying “yes” easy.
7. Don’t Bring in Your Baggage
I know we have all had those horrific dating stories, but when your conversations turn into a trauma dump of all your bad dates, that’s not going to turn anyone on.
Venting about your ex or listing everything you don’t want can start to make the other person feel like you’re an emotional vampire with all the negative chatter.
The deeper stuff? It matters, but save these hard topics (your past relationships, non-negotiables, your healing journey) for when you’re actually sitting across from each other, and trust has had a chance to grow.
The Fix: Focus on what you DO want. Show up with warmth and curiosity. Keep early conversations light, positive, and focused on what excites you and what you want to build with another person.
Up Your Conversation Game to Land More Dates
Here’s what I want you to remember: getting matches means you’re already halfway there. People are interested! Now it’s about showing up in the conversation the same way your profile shows up: genuine, curious, and ready to connect.
So here’s some homework for you. I want you to practice better conversational habits. Send a more personal opening question. Ask one follow-up question that sparks a meaningful conversation.
Or stop dragging your feet and get the courage to ask that match on a date. Remember to be specific! You’ve got this.
