This is getting annoying. I have such a damn habit of not wanting to hurt or disappoint people that I end up doing more damage. This is particularly troublesome with dating and relationships. Indeed, I decided to let things linger on too long in a couple of instances.

This happened most recently with my last LTR. It was apparent relatively quickly that it would just be a friendship. Three and a half years later, one Tinder incident and both parties rather burned out, it ended. Ironically, it almost ended a few months in and I should have probably let it.

Ultimately, my gut seems to be pretty spot on in hindsight. If it’s not feeling right early on then it’s time to move on. Why waste time waiting for something to happen that’s not going to happen. Why wait for things to “develop” or get better. Cut bait and go.

As blunt as that sounds we all know it’s not that easy. There are things that resonate with people that make you want to hang around and see if there’s more. It also legitimately takes time for relationships to develop. But what’s the window of time that should be given? When is the drop dead point?

I’m currently struggling with this again. The person I’ve been casually dating is nearly an hour away in most traffic. She also can’t drive on account of being legally blind and has dogs that need tending to so overnights at my place are pretty much out of the question. She has three kids which she has 75% of the time. Finally, her divorce isn’t final yet.

We’ve dated about three months, getting together barely once a week. Most of it my driving the hour, or half hour if she takes Uber to meet me, to see her. This is usually in the evening around bedtime so there’s essentially time for a drink, sex and spending the night together before I leave at 6 am to head home to get ready for work to feed my cat.

I’m just not into doing the distance, not to mention the level of conversation is not really where it needs to be. I’ve been on dates with other people where the conversation flows and is great. This is not the case here. There’s a lot of silence. The sex is good, but that’s only sex. There does need to be more to it than that.

I went to end it a few days ago, but was essentially talked out of it by her. Not only that I gave up some power in it and created the possibility for more hurt by talking about scheduling more activities together. I really don’t need more on my calendar! We ended up meeting mid-way for drinks and I drove her home. Then it was same stuff, different day.

Really she seems a lot like my affair person. Lonely and scared, going through an annoying divorce, libido is up as part of the coping mechanism and there are some small isms that feel like there’s some level of bullshit going on. When things are calm, conversation is forced or vacant.

Fortunately, I’m working through this. Getting a nudge and some help from my friends and therapist. I hate to cause hurt, but what I’m really doing is putting off hurt for bigger hurt. I’m also not being fair to myself letting resentment and anger fester until I boil and explode.

It might be worth some ground rules. Such as:

  • Making dating criteria hard lines: distance, education, situation all MUST be there
  • Trust my gut, after the first couple dates, if things aren’t feeling right, call it off
  • Be resolute. Make the decision and make it final. One date, that didn’t go anywhere called it the “fuck yeah” or “hell no” mentality
  • Hold off on sex. I love sex and have no shame or problems with sex during dating. However, I’ve found that making out like teens without the immediate horizontal naked time is kind of fun. Going all the way right away kind of kills some of the allure. Also, it helps make sure there’s a deeper connection than just physical.

Ending this current situation is going to be a pain in the butt, but I can and have to do it. There’s no point in prolonging the inevitable.

I still feel like I have much growing up to do. Sigh…