Yeah, introvert who's been working on social skills for the past decade, but hit a brick wall when it comes to making conversation more fun. Especially with women. If you put me in my niche (and male-dominated) hobbies/interests, you would mistake me for an extrovert. Put me together with regular people and it's a totally different situation.

"Get them to talk about themselves." Yeah, no problem. "Hook points." Yeah, no problem. Tease. Yeah, no problem. If they're an interesting person. Sadly the majority of people I meet aren't, and they don't give me enough material to work with. Even so, when I can keep a conversation going it's still too dry. This applies both to text and in-person.

I recently fired up Tinder about four days ago; tried Bumble too. Across both I got 33 matches. I only had natural, fun conversation with 3-4 of them. I don't know if those statistics are good or bad, but I feel like I'm shit at making conversation fun. The common things among those 3-4 were:

  1. She had pictures of active hobbies
  2. She had something interesting written in her profile
  3. She was proactive and contributed to the conversation

The remaining 29-30 girls? Generic pictures. Little to nothing in their profile. In fact, the vast majority of them had some variation of "No hookups/ONS/FBW" or "looking for serious relationship" yeah like that actually works. And they put little to no effort into the conversation.

"But texting is for logistics." That has never once worked for me here in Tokyo. There has always been a slightly protracted text game until the girl decides she's okay with meeting me. How protracted depends on the girl. But I digress.

So, what have I done to try and make my conversations more fun when the girl doesn't give me enough material to work with? Google. I see all these examples of random-ass questions like "What sums up your Sunday morning breakfast: a <insert whacky option>, b <insert whacky option>, or c <insert whacky option>?" My rectum is lacking in whatever organ creates these kind of questions, so honestly, where in the hell do you guys come up with questions like this? The best I've been able to do so far is, "So I've heard today is 'national slap your annoying coworker day'. Did you slap anyone today? haha" to which she replied "What" and immediately unmatched me. Now I'm worried the other five girls I sent this to will unmatch me.

So what's the secret to a fun conversation that isn't going to have me grasping for the 8-9% of girls I have a natural vibe with, because 8-9% is a terribly low number when the DTF girls are going to be an even lower percentage than that.

And slightly related question: Is Tinder Gold/Plus worth it? It claims I have 60 likes but I smell bullshit to get me to spend money...