What are the rules again?

What’s the best way to tell someone you’ve gone out on a date with that you’re not interested in seeing them again? And when is it acceptable to deliver this message, after the first date or the second? What about after the third date?

What if you’ve slept with them by the third date, can you decide then, or is that considered rude and bad form and now you should wait…?

But for how long?

Are there general rules that we should all be adhering to, one size fits all style, or is it a case by case thing?

Dating is hard. For all of us. Not just for you, not just for me, for all of us. But still, why do the somewhat simple things have to be so freaking hard?

I’ve been “dating” the last few months, and have tried to be kind and considerate, and careful with my words and my delivery when I don’t feel the “spark”. I am not a ghoster, and I promise that I never will be, because that’s a whole new level of wrongness. I’ve been the recipient of that practice more than once, and it’s horrible and inconsiderate.

The sting of it stays with you much longer than you would like, too.

I will not be mean or cruel, saying something rude or ignorant to deliver the message either, I have never been that way. I was not a “mean girl” in high school and I am not going to be one now as an adult.

I also refuse to use the old, steady, tried and true “it’s not you, it’s me” line.

It is definitely me.

I know it’s me making the choice, making this decision and speaking or texting these words. I am making it with full awareness of the end result, and I am good with that.


I have delivered this type of message only a few times over the last few months, basically deciding not to waste someone else’s time just to go out for another lunch/dinner/drinks. I don’t need to be entertained at some else’s expense, and honestly my time is valuable too, so I don’t want to waste days/nights that I am away from my family with someone that I don’t see a possible future relationship happening, even a short term one.

You’re welcome.

This isn’t a job search. I won’t be conducting follow up interviews or checking references. I don’t “need” to fill a vacancy, actually we’ve done away with that “position” and our company is much happier and more productive now! Thank you for your inquiry.

You would think that most men would be relieved to receive this news early on, in the beginning dating stages, before any real emotional attachment could happen, or is expected to begin.

You would be wrong.

I truly thought I was being a good, caring, considerate person by letting the other person know this, setting them free to pursue others and continue on with their dating life – online or otherwise. In other words, don’t delete your dating profile yet!!

It’s not even technically a break-up at this point, is it? So why is this so hard??

I have been met with not necessarily disagreement, more like disbelief and questioning of my sanity or my decision making ability. Really.

I have been told that I am making a mistake, and didn’t give it enough time to really know. We had gone on one lunch date, but prior to that had talked and texted for a couple of weeks before meeting in person. I knew his whole life story by then, the good the bad and the ugly, and thought that maybe this was a good thing. Less surprises down the line possibly? He seems open and honest, and that’s always a good thing, right?

Sadly, the in person interaction made the decision for me.

The details aren’t important, but I knew by the time I left that lunch date that I would not go out with him again. And it made me sad. Sad that I felt we had connected so well texting and talking on the phone, he seemed sensitive and caring and had a really good heart, but it wasn’t enough to support his in person version.

I was disappointed in the entire online dating process at this point.

Lesson learned? Don’t spend days/weeks (or months…that’s a whole different story) texting and talking to someone before meeting them. It creates a lot of build up, that will most likely fall flat when you do finally meet in person. Save yourself the trouble, and the invested time, and just meet for coffee for a quick assessment of chemistry. One hour at most. So much time (and feelings) saved that way.

I have learned…but that hasn’t stopped me from making other mistakes, obviously.

This one was pretty easy overall, a few texts later to politely explain and decline another date, and he backed off. We’re still in touch, on a friend level, which worked out better than I expected in the beginning. I was still pretty stumped by his reaction, but as they say, it could’ve been worse.

Which takes me to the latest one…

I did the initial quick drink date to get a feel for chemistry this time, and that seemed to go well, lasting longer than I expected in a good way, which lead to a second date. That also seemed to go well, a day spent walking the city and having lunch, we spent four or five relaxed hours together.

We had great banter, he called and texted equally which was refreshing and fun.

He was a little too “hands on” for my comfort level from the start, touching and kissing me as if we’d known each other much longer, but as usual I explained that feeling away by telling myself that it wasn’t necessarily wrong it was just different, and maybe I needed “different” this time around. Expressive affection shouldn’t be a deal breaker.

Another learning moment: communicate your boundaries. (Still working on this one.)

I found his acerbic sense of humor interesting and funny…until it wasn’t. It started to feel like an ongoing stand-up comedy routine that I was continuously being roped into playing along. Anything to keep us laughing, to highlight his sarcastic sense of humor, which can be just plain exhausting. Some of his comments about my life and where I lived started to have an edge to them, too. I tried to override the feeling, thinking I was over-generalizing his personality, so I agreed to a third date.

I have to say, I should’ve called it after the second date, I know that now.

He was obviously not over his last relationship, having just gotten out of a long term live-in arrangement only weeks before meeting me. His texts were getting more and more personal and uncomfortably intimate within a couple of weeks, which should have tipped me off, but I still carry a few old habits of going along with the program to be nice, and trying not to be too quick to make a character judgement. I also get caught up in the idea that maybe I am over-thinking things, thanks to many friends and family telling me so over the years, and I convince myself to just relax and let things play out.

Ignoring my gut, basically.

But a third date was on the books, at his apartment for dinner. I knew what that meant, I’ve googled enough dating coaches and websites to get the gist, but I went anyway figuring I would cross that bridge when I got there.

I crossed it alright…

Another learning moment, I am no longer the young twenty-something who “owes” anyone anything. Time to stop this guilt train that leads to regrettable sex. Ugh.

So, I had to find a way to tell him that I no longer wanted to pursue this relationship. Only three dates in, but now I’ve complicated things with sex.

But, wait a minute…don’t guys do this kind of stuff all of the time?? This shouldn’t be a big deal to him, should it?

ummmm…yeah, I guess it can be.

After a half hour phone conversation I couldn’t bring myself to say what I was thinking because again, banter and laughter, that lead to a long polite text explaining why I no longer wanted to see him, which lead to another phone conversation that ended with him telling me he wouldn’t “try to change your mind”.

That’s a relief…or so I thought.

He proceeded to text me every couple of days afterward, with snarky comments about setting him up with single friends in my neighborhood (I don’t have any single, unattached friends in this state, by the way) or to tell me that I “owe” him a drink at the brewery we went to on our first date.

Owe him for what?? For not wanting to see him or sleep with him again?

I answered politely to the first couple of texts, because I am not a total bitch, but then it was beginning to feel aggressive and pushy. He wanted to set up a date for a drink – I thought we had covered this idea, that I no longer wanted to date him?

After the first few texts, and some coaching from my single friends (in other states), I stopped responding. Essentially, ghosting him. Ugh.

This is so not who I am, or who I want to be, but left without many other feasible options it seemed to be the best idea. It worked, thankfully. (knock on wood…)

Dating is hard enough, and stressful enough, at any age but I will add that in our later years it carries a lot more baggage with noticeably different expectations than we had in our twenties. Not to mention that some of us are starting from square one, usually after a very long hiatus in a longterm marriage, leaving us feeling very naked, unprepared and incredibly vulnerable in this arena.

The main rule in dating should just be basic social etiquette.

Be kind, be considerate, be honest. Accept when things don’t work out and move on to the next opportunity, without malice or guilt inducing conversations.

We shouldn’t need a slideshow presentation to get that point across.





2 responses to “What are the rules again?”

  1. aintlifegrand101 Avatar

    Oh girrrllll- welcome to the party. I see in your musings here so much of where I’ve been and am. A couple of thoughts to encourage you. You weren’t ghosting that last guy. You said your truths. He didn’t honor them. It is completely noble all the communication you gave him. More than necessary. Umm so much here! I just wrote a post last week about being a nurturer. https://yearofsluttery.com/2020/10/08/a-bad-combo-writer-bitch-nurturer/
    These guys are tougher than they act and you have no responsibilities to them, none. You are dating honestly and authentically. You rock. Listen to that gut and say your truth and they will think you a “bitch.” You aren’t. Or maybe we need to take that word back. I’m not so sure it bad to be a “bitch.”
    Looking forward to reading your journey. I think you will laugh and commiserate with me on mine. Go back to April 2019 to start. You’ll laugh your ass off.

    Liked by 2 people

    1. somebodyssister Avatar

      Thanks for the encouragement and the honesty, so relieved to read experiences from another in the trenches of this dating game. I love your blog and am basically using it as a coaching tool in many ways, along with a list of online dating coaches I have started absorbing through YouTube videos – oddly enough they’re all aimed at women and how to handle the challenges of dating in these times, hardly any videos for men to learn the same…maybe because they wouldn’t use it/listen to advice anyway?
      I will def go back and read your earlier stuff, it’s all part of the process isn’t it? I’m sure I’m on a similar path as you, just a few steps behind possibly, learning as we go 🙂

      Liked by 1 person

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