Hey everyone, I’m in a bit of a bind and could really use some fresh perspectives. I tend to overthink things and get super insecure about making new friends, so I could use a little help here.
So, here’s some backstory: My best friend—we'll call him Henry—has been in my life for almost a decade. Henry's parents are divorced, which means he's been living a double life, splitting his time between our town (where his mom and I live, and where we went to school) and a nearby village (where his dad lives). Henry’s always kept his “town” and “village” friends separate, kind of like two secret identities. In our country, the town-village divide is a big deal, so it’s not really unusual.
Recently, my car decided to take an unplanned vacation and broke down. To add insult to injury, the guy at the parts shop was so condescending, I almost walked out without my new battery. Henry, who’s got some serious mechanic skills, had been my go-to guy for car advice. In the midst of dealing with my car troubles (and the parts shop guy), I asked him if he could teach me a few things about fixing cars myself (because I didn’t want to go to a parts shop again with just forum/wiki knowledge). To my surprise, he didn’t just agree—he invited me over to the small repair garage he runs with his best friend. And that's where the story begins.
So, that’s when I first met Henry’s best friend—we’ll call him Ricky. Ricky turned out to be a really cool guy. We hit it off immediately, cracking jokes like old pals. I had been worried all day about being awkward or making a bad impression, but it was all for nothing. The vibe was great, and by the end of the night, Ricky invited me to join him, Henry, and a few of their friends for drinks the next day.
Here’s where things got a little weird. While we were working on the car, Ricky was under it doing his mechanic magic, and I was playing the role of Tool Runner Extraordinaire. As I passed by Henry, he whispered urgently, “Say no to the invite. Don’t come.” I was a bit confused but did as he asked.
This happened not once, but twice more. Each time Ricky invited me to join them, Henry swooped in with a clandestine “Please don’t come.”
The final straw came last night. Henry, Ricky, and their crew were on a road trip to Croatia for some scuba diving training. After their 16-hour journey, the duo managed to find some signal and called me for a chat. We were joking around, everything seemed fine, and then Ricky asked what I was doing on the 28th. I mentioned I had no plans, and he immediately invited me to his sister’s birthday party. He was super excited and persistent, saying things like, “Great, you’re coming!” He even teased me about my supposed inability to hold my liquor to convince me. (Which is a real insult in our country).
While Ricky was enthusiastically trying to rope me into the party, Henry was silently texting me on Messenger with one-word pleas: “No. Don’t.” Desperate and confused by Henry's insistence, I blurted out, “Look, even though we’re getting along, I’m not a 100% fit in your world yet.” I meant it as a tease, not really meaning it, and Ricky took it that way, but the conversation felt a bit strained afterward.
After the call ended, I felt like a wreck. I texted Henry, laying it all out: I knew he disapproved of me joining their hangouts, but I didn’t want to jeopardize my budding friendship with Ricky. I told him he needed to explain to Ricky why I couldn’t come or give me some clue as to why he was so adamant. Honestly, I was terrified I had messed things up.
Henry's reply came in while I was typing this post: “You can come at your own risk.” Passive-aggressive much? It’s like he was warning me about entering a social minefield without a map.
I get it, though. Ricky’s been Henry’s best friend for almost twenty years. I don’t want to be a burden to either of them. I understand that parties, hangouts, and the expected behavior are different between town and village life. I know I’d probably be judged by the other folks, and I don't want to be the person they have to babysit. Or be the one because of which Henry would like he has to behave in a certain way because I am a town-girlie and be constricted by it.
So, what should I do? I need your thoughts and advice on navigating this tricky situation without making things even more akward and why Henry seems so keen on keeping me from joining their outings?
TLDR: My (20F) best friend Henry (20M) has been keeping me from joining his hangouts with his village friends, including his long-time buddy Ricky (20M), even though Ricky and I get along well. I’m torn between respecting Henry’s wishes and not wanting to mess up my new friendship with Ricky. Looking for advice on how to navigate this tricky situation.