If you’re new here — I’m Amanda Carroll. I’m a dating strategist and former national radio host, and I’m the personal dating coach for women who built a career they’re proud of and never got a plan for this part. This Substack is your playbook. One play a week. You study it, you run it, and you stop guessing at the one area of your life you’ve been running on instinct.
There is a particular kind of dating heartbreak I hear about all the time.
It’s not just, “He broke my heart.”
It’s “I can’t believe I spent five months figuring this out.”
Five months before you realized he wasn’t actually ready for a relationship. Five months before you noticed you were doing all the planning. Five months before you discovered that the man who described himself as a “great communicator” could communicate beautifully right up until you disagreed with him. Five months before you finally admitted that his words and his behavior had been telling two completely different stories.
And afterward, you look back and think:
How did I not see this sooner?
I have a theory.
Sometimes you didn’t need more time.
You needed better information.
And if that sentence just hit a little too close to home, this is exactly what we’re fixing inside Dating Reset Training Camp, which starts TOMORROW.
For three days, I’m teaching you how to stop spending months trying to figure out whether a man is right for you and start knowing what to look for, what to ask and what his behavior is actually telling you.
Three days. $47. We start tomorrow.
→ JOIN DATING RESET TRAINING CAMP
We’ve Made “Give It Time” a Dating Strategy
Think about how often women are told this.
Give it time.
Maybe he’ll open up. Maybe he’ll become more consistent. Maybe he just needs to get comfortable. Maybe you need a few more dates. Maybe you’re being too picky. Maybe you’re expecting too much too soon.
And listen, I am absolutely NOT suggesting that you can know everything about a human being after five dinners and a couple of margaritas. 😂
People unfold over time. Trust develops over time. You absolutely need time to observe someone in different situations.
But there’s a big difference between allowing a relationship to unfold and waiting for time to make your decisions for you.
That’s where I think women lose months. Sometimes years.
Because if you don’t know what information you’re looking for, you can go on 25 dates and still not know much more about whether this man can actually be the kind of partner you want than you did on Date Two.
You know his favorite restaurant. You know what happened with his ex. You know he hates cilantro and wants to go to Italy. You know he thinks you’re gorgeous.
Great.
But what have you learned about his capacity to be your partner?
That’s a completely different question.
And it brings me to one of my favorite new Plays.
THIS WEEK’S PLAY: THE FIVE-DATE TIME MACHINE
I wish I could actually put you in a DeLorean, send you back to Date Two with your ex and whisper, “ASK HIM ABOUT THAT.” 😂
Sadly, I do not currently have access to a DeLorean.
But we can do the next best thing.
We’re going to use one of your old relationships to figure out what took you months to learn that you could have started learning much sooner.
And I want this to be fun.
This is not an exercise in beating yourself up over everything you “should have known.” You know what you know because you lived through it.
Now we’re going to use it.
Consider your dating history game film.
We’re reviewing the tape, finding the clues you missed the first time and making you a much better player for the next game.
Here we go.
STEP 1 — Pick the Man
Choose one past relationship or situationship that lasted long enough for you to eventually discover something important about him.
You know the one.
Maybe it took you six months to realize he wasn’t actually interested in building a life with anyone. Maybe you eventually realized you were carrying the entire relationship. Maybe he loved talking about emotional intelligence but couldn’t handle conflict. Maybe you discovered he had no real direction. Maybe you spent months believing his potential instead of paying attention to his reality.
Pick ONE man.
And before we do anything else, no rewriting history to make yourself look smarter. 😂
We’re looking for information, not prosecuting your former self.
STEP 2 — Start at the Ending
Finish this sentence:
“By Month Five, I knew ________________________.”
Or Month Three. Month Eight. Year Two. Whatever your timeline was.
What was the thing you eventually knew that changed how you saw the relationship?
Be specific.
Not: He wasn’t right for me.
What did you actually learn?
He said he wanted marriage, but his life wasn’t moving toward partnership.
I was always the one making the relationship happen.
He avoided difficult conversations.
I couldn’t depend on him when something went wrong.
He liked having me in his life more than he wanted to build a life with me.
That sentence is the information it took you months to collect.
Now we’re getting in the Time Machine.
STEP 3 — Go Back
Ask yourself:
When was the first evidence actually there?
Not when you finally accepted it. Not when the relationship ended. Not when your best friend finally said, “I love you, but COME ON.” 😂
When did he first show you?
Go backward.
Was there something on Date Three? Something he said on Date Five? A plan he never made? A question he avoided? The first small disagreement? The first time you needed something? The first time his words and behavior didn’t match?
Or maybe it was the first time you caught yourself explaining something away because everything else felt so good.
This is the part of the exercise that can be a little shocking.
Because something you think you learned in Month Five may have first shown itself in Week Three.
You just didn’t know yet that it was information.
And THAT distinction matters.
STEP 4 — Rewrite the Date
Now ask:
What could I have asked, observed or done that would have helped me understand this sooner?
Notice I didn’t say, “What question could I have asked that would have forced him to reveal his deepest character flaw over appetizers?”
That’s not dating. That’s an FBI interview. 😂
And men can give wonderful answers to questions.
We’re interested in answers and behavior.
Maybe you needed to ask a better follow-up instead of moving on because you liked his first answer. Maybe you needed to stop making all the plans for a minute and see whether he stepped forward. Maybe you needed to state what you wanted clearly and watch what happened next.
Maybe instead of asking, “Are you looking for something serious?” you needed to become curious about what his last serious relationship actually looked like.
Maybe you needed to stop asking whether he said communication was important and start watching what he did when communication became uncomfortable.
You’re not trying to expose him.
You’re giving yourself opportunities to see him.
And now comes the most important question in the entire Play:
What are you currently waiting for time to tell you that you could start learning now?
Sit with that one.
Because if you don’t know HOW to answer that question yet, good.
That’s exactly why I created Dating Reset Training Camp.
The Five-Date Time Machine helps you see what you missed in the past. Dating Reset Training Camp teaches you what to look for while you’re dating NOW.
We start tomorrow. It’s three days, it’s $47, and I’m going to teach you the strategy I wish every woman had before she gave another six months to the wrong man.
→ SAVE MY SPOT IN DATING RESET TRAINING CAMP
Dating Is Not a Final Exam
I think part of the reason dating feels so exhausting is that women walk into every promising date carrying one enormous question:
Could this be my person?
That’s a LOT of pressure to bring to cocktails.
No wonder dating stops being fun.
What if you didn’t have to figure that out?
What if your job on Date One wasn’t to determine whether you’ve found your husband?
What if you were simply curious?
Who is this man? What am I learning? Do I like how I feel around him? Are his words and behavior lining up? What happens when things don’t go perfectly? Do I want to know more?
Then at the end, you make one much smaller decision:
Has he earned another date?
That’s it.
You don’t need to know by Date Five whether you’re going to marry him.
You need to know whether he’s earned Date Six.
And if he has? Great.
Go have Date Six. Learn something else. Have fun. Flirt. Eat the pasta. Kiss him if you want to. 😂
This isn’t about turning dating into a clinical evaluation where you’re sitting across from a man with a clipboard assigning points to his conflict-resolution skills.
It’s about making dating lighter because you’re no longer trying to predict the ending.
You’re simply getting better at making the next decision.
THAT Is How You Compress Time
When I talk about knowing in five dates instead of five months, I don’t mean you’ll know everything about him.
You won’t.
I mean you can become dramatically better at identifying whether the man in front of you deserves more of your time.
Because time isn’t neutral in dating.
Every additional month creates more attachment. More memories. More chemistry. More physical intimacy. More hope. More reasons to explain away something you might have evaluated much more clearly at the beginning.
So my goal isn’t to help you date faster.
It’s to help you learn faster.
That’s a very different thing.
And once you learn how to do that, dating can become a lot more fun.
You’re not wandering around hoping the relationship eventually gives you an answer.
You’re participating.
You’re curious.
You’re watching.
You’re choosing.
Want to Stop Finding Out in Month Five?
This is exactly why I created Dating Reset Training Camp.
We start tomorrow, September 15, and for three days I’m teaching you how to stop dating by chemistry, hope, potential and “let’s see where this goes” and start dating with a strategy.
Because I don’t want you becoming better at getting men to choose you.
I want you becoming extraordinarily good at choosing them.
We’re going to work on what to look for, what to ask, what deserves another date, what you’re explaining away, how to separate chemistry from compatibility, and how to recognize much earlier whether the man in front of you has the capacity to be the partner you actually want.
The goal isn’t to decide whether you’re going to marry him in five dates.
The goal is to stop spending five months gathering information you could have started gathering in five dates.
That’s the time compression.
That’s what I want to teach you.
Dating Reset Training Camp
September 15–17
3 days | $47
And we start TOMORROW.
→ JOIN DATING RESET TRAINING CAMP
RUN THE PLAY
Sometime today, give yourself 15 minutes.
Pick the man.
Finish the sentence:
“By Month Five, I knew ______.”
Then get in your Time Machine and find the first clue.
When did you actually start getting that information? What did you miss? What did you explain away? What could you have asked? What could you have observed?
And most importantly:
What will you do differently next time?
Because your past dating experiences weren’t wasted time if you learn how to use what they taught you.
They’re game film now.
Study them.
Then get back on the field.
Dating doesn’t have to be miserable. It doesn’t have to take over your life. And it definitely doesn’t have to take five months every time you need an answer.
You don’t always need more time. You need better information.
Run the Play.
Amanda
P.S. If there is a man in your past you spent five months—or five YEARS—trying to figure out, don’t do that again. Come to Dating Reset Training Camp. For $47, I’m going to teach you how to get better information sooner so you can stop wasting your time on the wrong men and start recognizing the ones worth choosing. We start tomorrow.