TIFU by being awful at flirting.

Disclaimer: this happened a year ago.

I (30F) decided to go on a long hike in an area I’m slightly unfamiliar with. Along the hike I kept leapfrogging a group of three with an adorable pup. I kept hearing the guy running point on the hike call the dog back as it wandered off trail, and the name sounded close to mine. By the third time I leapfrogged the group, I was able to discern that it was made up of a romantically linked couple and a single guy. I got a look at the guy and thought he was pretty cute. Now Reddit, I am notoriously an awful flirt. I get incredibly flustered and self conscious when trying to do it, so I’ve been challenging myself to start to talk to people I find attractive. l paused and asked “hey! Is your dog’s name x? Mine is too!” Confused, the guy turned and looked at me like I had three heads. He then replied, telling me a name that sounded NOWHERE close to my name. Strike one.

Since they seemed like they knew the area pretty well and had a map, I decided to try again and ask for directions to a small peak nearby I wanted to summit. The guy nicely obliged but I didn’t get any hints of continued conversation. Not wanting to interfere with the group’s time together, I carried on my way. Come to find out, it was the same hike the group was doing, so once again, we found ourselves stopped at the same location at the peak. There was a little shelter I was resting in, and they eventually came to pause there as well, so I tried to strike up conversation again. This time I focused on trying to pet the dog and asked polite questions like where they’re from, etc. The dog kept wandering over to me, sniffing - I presume to see if I have food, so I say “sorry bud, I don’t have anything.” Conversation is going well with the group and the guy of interest, but I’m still incredibly flustered. A few minutes after I made the comment to the dog, the guy gets out my favorite fruit snacks and offers me one. Now Reddit, this would have been a great time to say “yes, thank you!” and move to sit closer to the guy I thought was cute. But MY stupid brain instead thought “say something witty and funny” so instead of doing the logical thing I say “I was talking to your dog, not you” with a grin on my face. Mind you, this joke made sense to my flustered brain at the time. But objectively speaking, WHAT?! How is someone supposed to take that?? WHY is that what I defaulted to? Strike two.

He seems a little off put and pockets the gummies while I, now realizing what a dummy I am, excuses myself to continue my hike. Because frankly, there’s no coming back from that. I thought to ask them to join their hike, but after that interaction, I thought better of it.

As I’m heading down the trail from the peak, I hear him calling the dog again. I turn around, and he’s trotting after me. He runs up to me to get the dog with an apologetic smile. Which, would have been a great time to ask to join them, but I was still too embarrassed.

We leap frog some more while I stop to take photos of the landscape and they do the same, and I FINALLY get the gumption to ask the woman in the group if I can join. She agrees and I start to believe I can redeem myself and finally get some conversation in with the guy.

Her and I chat for a while as we hike down the mountain. She keeps referring to her brother and saying “oh you should ask him about his travels here” and “oh my brother is totally like that too” and so and so. And it’s getting to a point in conversation where it’s relevant to naturally bring him into the conversation when I look down and realize that somewhere along the trail, I dropped my phone - while being alone and far from home.

I already felt like I intruded a little on the hike, and I didn’t want to be a bother to them and ask for their help.

So once again flustered, I mutter that I lost my phone, quickly apologize to the group, and sprint off up the hill. I eventually found it, but I never caught up with them again. Looking back, I could have asked for their help, asked for someone to call it - SOMETHING that was engaging more of the group and the guy in question, but instead, I literally just sprinted away without even letting them offer. Strike three, and I’m out.

Reddit, if you EVER are hard on yourself for your inability to flirt or pick someone up, take comfort that it can’t get much worse than my failed attempts.

TL;DR: I have multiple softball opportunities to flirt with someone I found attractive. I botched every single one then ran off in shame