How Do I Get Better at Dating?

Sep 30

Kumusta Tita,

I just made a fool out of myself trying to talk to another guy (25 male here) around my age. I get so anxious about what I’m saying, and if I’m saying too much about myself, I just can’t feel confident in person. I also haven’t had a date or just someone to talk to that is also a gay/bi male in maybe 5 years. This has been troubling me lately because dating or getting into a relationship has been what I have been working towards since after high school. What I’ve been doing hasn’t worked.

So I’m wondering how do you start off with talking to someone? How do you deal with the flow of the conversations? How do you respond to the other person especially when they don’t continue the conversation? Do you filter what you say? Do you ever disclose that you are a shy person or that you’re inexperienced? Where do you get your dating/relationship experiences from or where do you have the most luck? Since I’m from a small town in the Midwest, should I move to a big city?

Sincerely,

Lonely Farm Boy

Hey LFB,

If you’re gonna ask me how to start talking to someone, you would have an easier time asking me how much water we should be drinking per day. I would not be able to give you an accurate answer as I’m not really sure myself. It’s quite interesting that nobody teaches us how to socialize as adults. When we’re not in a school setting, we don’t have that context of forced group work, a shared disdain for the same teacher, and mutual interests in which Pokemon cards we want to trade. (Is that still a thing with the kids?)

Finding connections as an adult is hard work because you have to make a conscious effort to create these relationships. In the age of TikTok, I’m pretty sure you can find community in whichever part of the world you’re in. You may have to work a little harder to find those pockets of society that have the same interests as you, but I promise you that you will be able to find a group. And once you find that group, that’s how you can practice starting a conversation because now you’ll have something in common to talk about.

Dealing with the flow of conversation is a different beast. Again, there’s no masterclass on how to talk to a person. All the socializing lessons I got were from Sesame Street, and that barely covers the gamut of human interactions and doesn’t go beyond your please and thank yous and laughing three times after every number. Keeping with the flow of conversation isn’t meant to be a mental gymnastic feat. Once you get to talking about what you’re interested in, I find it helps to keep the conversation going when you ask lots of questions about the small details in what they’re saying. This usually leads you to a tangent which then leads to more conversation! My nightmare scenario since I need us to stay on target, but this could be good practice for you, LFB.

If you can’t think about how the conversation can flow naturally, try small talk. Personally, I’m not a fan. It makes my skin crawl and my eyes roll to the back of my head if someone strikes up a conversation with me about how the weather has been too hot or too cold and it’s never just right. Like, really, George? Are you so inconvenienced that you have to wear a windbreaker in the morning and then have to carry it with you for the rest of the day? God, just put me out of my misery and lobotomize me. But if you find that you’re at a loss for conversation topics, a non sequitur can go a long way from when you can no longer talk about Dungeons and Dragons and then switch to how awful traffic has been lately. And if they don’t want to talk about that either, guess what? It’s fine to end a conversation right there. Normalize saying, “I’m good for talks now. Thanks!”

Being a pseudo-public icon, I am always filtering what I’m saying in that I filter out nice stuff and leave mundane droll for content. I am great at public speaking and podcasting, but I suuuck at conversing. I find that I’m great at talking for the purpose of content creation, but I’m not too keen on talking in social settings. I may have psychopathy, but I’m too scared to get diagnosed for that because it’s probably true. This is a skill that I continue to practice in my social circles, and Imma be real with you, LFB — it’s hard. Even in a social setting, I filter out what I have to say because my goal becomes focused on wanting to make other people laugh. I’m essentially making content on the spot and not making conversation for the sake of connection. But you sound like you want a genuine connection instead of testing out your tight five, and I bet that people would appreciate that about you even if you are a shy person. In fact some people find it endearing and charming that you disclose your shyness. That allows them to take the lead and you can follow their rhythm. On an unrelated note, are you a bottom?

Considering that you are a small-town boy and all the things I’ve listed so far are quite reliant on more people, you may find it easier to get more experience in a bigger city. I’m not trashing on rural life. In fact, as a person who lives in a big and densely populated city, one of my dreams is to just throw this all away and move to a farm and tend to the land without ever being disturbed by the outside world. Nothing would make me hornier than to just get off the grid. And you sound like you’re the opposite. Grass is always greener, right? You’ll find more diverse experiences and more gays living in bigger cities because that’s where all the action is. Gay life survives in rural areas, but gay life thrives in the metropolis. You don’t have to move if you love living where you are. But maybe you can try staying in a big city for a month or two and see what kind of life you can cultivate from there. Get ready to find lots of events that you’ll say yes to but never end up going because some hot guy decides to hit you up at the very last minute on Grindr. You can join a book club, a knitting circle, find a gym buddy, try speed dating, or just dance at a gay bar and see where the night takes you. The possibilities are endless when you have all these experiences in the palm of your hand in the big city. Just be sure to always wear protection. I don’t, but do as I say and not as I do.

Human interaction can be intimidating, boring, exciting, and nerve-wracking all at the same time. It’s such a hassle to create relationships and when you do find one you enjoy you are devastated when you lose it because you’ve worked so hard to create it. The beauty of that is that you get to restart and create something different, something new. You don’t have to confine yourself to your immediate surroundings not that we’re connected more than ever in the age of the internet. You are capable of finding love and companionship wherever you are in the world. You just have to know where to look.

Just don’t go looking for love in the gay village until you’ve had a tetanus shot.

Mahal kita,

Tita Slut