I’ve been talking to a former coworker for the past few weeks. We never interacted too much while we worked for the same company so a lot of our convo is just getting to know each other. The few times we did talk I felt a bit of chemistry with him.

At times it feels a little like an interview but from my past dating experiences, it takes a few months of talking to someone before I can talk naturally. I kind of force myself through this process because I’m super shy (and he is too) and I thought this was normal. We have moments where the conversation feels natural and great but other times when it seems like there isn’t a lot to say.

I keep seeing stories of SO’s meeting, and they always say that they immediately talked nonstop all day and all night, but I haven’t experienced that ever. Is it just because I’m shy or does it sound like I’m not a good match with the guy I’m talking to?

4 comments
  1. It’s because you’re shy. That’s all.

    Pretty hard to have “naturally flowing” conversation when you’re afraid to… ykno… conversate.

  2. Not everybody is a great texter. I would recommend actually setting up a date and see how the conversation is in person.

  3. Am I understanding you to mean that you’re trying to get to know each other solely via texting?

    Yeah, you need to make it mostly real life interactions, or at least phone calls. Texting is a great convenience re: imparting information, but is not a great thing with which to actually build a relationship or get to know a person if that’s the only way you’re trying to communicate.

  4. It’s normal for shy people, yes. You’re fine.

    I used to be painfully shy. When I talked to a guy, I would put them on this pedestal like they were cooler, smarter, and funnier than me, and I was basically a nobody reaching for things to talk about.

    You basically have to reframe your brain when you talk to them. They’re human beings, they’re not transactions – meaning, you don’t need to accomplish a checklist of questions in order to have a conversation. Thats not a conversation.

    Having a conversation should feel natural and flow. And that starts by putting your wall down, treat them like your dad or your mom, (might sound strange but go with me) and start naturally talking about your day. Get them off that pedestal. Then, when the timing is right, add some humor. Add some flavor to the conversation. Add some flirtation, and interest, and be your cool, unique self! Because I promise you, he can find a million other chicks to have a boring monotonous conversation with. Don’t add yourself to that list. Be the one who really stands out. Let me give you an example:

    Transform some of your texts to be a little more flirtatious. Use a few emojis that are different from smiley/laughing faces. Take a picture of what you’re doing currently. Let’s say you’re watching TV. Talk about the premise of the TV show, and keep that conversation going. My conversations with people always trail off onto other topics, whether that be a deep discussion or a funny silly banter about something that doesn’t matter.

    You got this! You can message me if you need help with a specific conversation.

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