The Deal You Make with Your Future Self

Red Flag Moments

Have you ever looked back at red-flag moments and thought "I should've broken up right then"?

The "should've" in there is so telling.

It's not just regret—it's recognition. That quiet voice in hindsight saying:

I've been there more times than I'd like to admit. The most recent one was expensive and cost me four years and a lot of money with an ex-girlfriend I'll call Sarah. After our first date, there were clear signals: mixed messages, odd behaviors, and cognitive dissonance between what she said and what she did.

My gut screamed, "RUN!" But I ignored it. I told myself it would get better, that I was overthinking, that giving her just one more chance couldn't hurt.

Fast-forward to a recent dating situation that feels eerily similar. I connected with someone—let's call her Denise—after a strong first date. She was fun and funny, interesting and very cuts. We texted back and forth a ton, shared photos, and built real excitement.

We had an upcoming second date planned. She tells me that she's really excited about our second date. We've spent about 6 hours on the phone in the last 4 days.

But, tonight - one day before our second date - she has a first date with a different guy. She says that she had already scheduled it with him. Not completely true as it was actually supposed to be last night (Sunday).

Now, we have only been on one date. I get that. But man, we have spent a tremendous amount of time getting to know each other, texting and etc. One of my boundaries after being married for nearly 20 years is to never be someone's option. Even if it is in the getting to know you stage. I mean, I know me. When I like someone, I elminate ALL other options because I don't want them to be a distraction from the person I like. It isn't commitment other than to myself. I commit to me to be undistracted by other women while pursuing a woman I like. Women claim to want to be pursued. Well, I pursue. And I am not distracted like a squirrel by others during that pursuit.

When I found out about the other date, I made a decision based on the deal I made with my future self. That deal was that when I see red flags. I will act on them RIGHT THEN. I won't simply brush them off or ignore them. Maybe you - the reader - doesn't see the red flag. That's okay. For me, however, the deal breaker is that I want to be someone's first choice.

An easy thing to do would be to raincheck the other guy. Especially because she said to me that she has "very strong feelings" for me. (after I told her that I was calling off our 2nd date)

My question is this. If you have "very strong" feelings then why risk going out with someone else, even in the early stages? I go on a lot of dates. 99% of them fail. There isn't a spark, or I get catfished, or whatever. But if I like someone, I stop ALL other dates, until that woman - and the possible relationship - is no longer a possiblity.

Tonight, as I write this, she is on that first date with the other guy.

Cognitive Dissonance

Today, while giving her a quick rundown of my decision, she showed me her cognitive dissonance. She promised investment in us, but her actions - going on a date with another dude - say otherwise. Her actions say my "options are still open."

What would my past self do?

My past self would've rationalized it: "It's early, she's just exploring, don't be rigid." But this time, something shifted.

I started hearing from my future self. And my future self doesn't want me to put up with any bullshit.

My future self isn't a distant, vague version of me. That "self" is a teammate in the ring with me right now. [TAG]

That future self is the one who lived the "Sarah" years. He's the one who paid the price in time, money, peace, and self-trust. He knows what it is like to invest four years of life and a shit-ton of emotional support to get nothing in return.

He's watching me right now and he knows exactly how these "small" overrides compound into big regrets.

And he's saying:

So I made a deal with him.

My deal with my future self is simple: When the red flags appear—especially the ones that echo old patterns—I pause and ask,

If the answer is "walking away before the costs pile up," then that's the move. No negotiation. No waiting to see if she'll change mid-date. No hoping the emotional plea ("Don't quit just yet") will magically align her actions.

For tomorrow's 2nd date, I cancelled. I stepped back. I waited to text her about my cancellation until her date tonight had ended because I didn't want to be reactive and intrusive. I waited until the evening felt neutral, then sent a calm, clear close: no trip, no continuation, wishing her well.

Boundaries upheld. Pattern broken.

You see, boundaries are not a cage for the other person. They are a deal you're making with your future self. A deal that, if kept, will reap benefits for me in the future.

My future self isn't directing me to be cold or perfect. He's asking me to tag him into the ring when I am unable to see that I about to get fucking knocked out by another relationship. He tags in to fight against the very real emotional pulls that show up in early dating (and relationships): the hope, the chemistry high, the joy of the new girlfriend. All of those things can be nasty distractions to the problems that are evident - even from the get go. My future self is protecting my time. My money. My feelings. My investment.

Those emotional "Pulls" come often in the context of new relationships or even current ones. Tag your future self into the fight. Listen to the questions your future self will ask you. And picture your future self stepping into the ring with you with all of his battle scars from the last time you ignored the red flags. He's got the proof. You fucked up last time. This time, he is ready to have your back and remind you of these things:

• Actions speak louder than words (even when the words are sweet and reassuring).
• People do what they want to do (not what they say they want when it's convenient).
• You can't make great chicken salad out of chicken shit (no amount of optimism turns bad ingredients and mismatched priorities into a delicious recipe).

The partnership of you and your future self isn't about shutting down vulnerability—it's about protecting it. It's about refusing to spend years paying off a debt you don't have to incur in the first place.

Sarah was a huge mistake. Denise could be too. My future self doesn't want me to date Denise.

The next time you spot a red-flag moment that makes you think "I should break up right then," listen. Make the deal. Let your future self tag in and say,

Because when you do, the "should've" becomes "I'm glad I did."

What red-flag moment are you looking back on right now? And what would your future self tell you if you could rewind? Leave them in the comments. I read every one of them.