I have tried conversing with people be it in the gym and even my friends from college or even work. I always feel like there is a ceiling I hit. I become a good hi-bye friend with anyone – basic small talk, relevant topic related conversation. I shine in these – which is why I have very ideal workplace relationships.
Problem is when it comes to a casual setting, I can’t seem to progress beyond a point, wherein I can’t get closer to people. I have no clue how to move into deeper conversations. I have tried asking questions to even friends I have known for 2 to 3 years, but I have observed that all of them are happy to spend time, go out and do fun things with me but not really sit and talk, because there is just awkward silence.
For this reason, I haven’t been able to build close or strong relationships with any person and it’s frustrating. I have been to multiple dates with women the last few months – all of them seem to be into me on the first date, we even make out and all but I’ve not been to a 3rd date with anyone in the last 2 years. They just seem to lose interest in me. Any thoughts?

9 comments
  1. More practice! It doesn’t come easily for a lot of us so observe others who do it well and practice. Also develop your own interests and talk to others who share them. Works for me.

  2. The first aspect is linking. Taking what they say and linking to it with a relevant comment, question or insight of your own. The second is being able to have tidbits from your own life to share, that comes from NOTICING what happens during your week that might be interesting, informative, entertaining, funny, heart-warming, frustrating, whatever it is. Usually comes from emotion or a human interest element. Doesn’t need to be a huge story! Just something that struck you as something fun to share. Write these down so you have a bank of fun topics to draw on. Review your list before heading out.

    When it comes to having a great conversation a lot of it is the VIBE with which you have it. In other words, showing a bit of passion for: yourself, the other person, and LIFE ITSELF. This is the part where people CONNECT, they hit it off, etc. (I suspect you’re good with the linking part, maybe not so good with the vibing part). In order to vibe well with people you have to bring some enthusiasm/passion/joy for life.

    E.g. they tell you something, is your response “Oh, that’s nice” (kinda monotone), or “WOW, that’s GREAT, I’d love to hear MORE about that.” Passion/enthusiasm really make a conversation sing.

    And you really have to practice developing that attitude within yourself, inside your heart, for it to be genuine.

    Also for deeper conversations people will often reveal something a bit personal, just avoid going too deep too soon. No trauma dumping!

    To increase your vibe I suggest working on a list of things you’re grateful for, doing a daily pay-it-forward exercise, and start speaking more enthusiastically OUT LOUD around your house when you’re home. To your pet (if you have one), or to your houseplant if you don’t. NARRATE some of your daily activities in an enthusiastic sports announcer voice. Get used to the sound of your own voice bringing more passion to yourself, to your life, then bring it to the WORLD.

    That’s where I’d start.

    Good luck!

  3. It’s okay. Keep doing so and keep working on yourself. You’ll eventually click with someone. In the meantime just keep having fun and stay delightful to be around people.

  4. Remember when catfishing was a popular thing? Yeah… those trust issues are hard to work with.

  5. You and me both. Makes me feel like I just lack depth as a person and have nothing interesting to share beyond how work is going or the latest Netflix series.

    I am trying to pay closer attention to myself to try and figure out why I struggle so much to make closer bonds, and part of it has to do with me never sharing anything personal and basically refusing to talk about myself. For example, I noticed how when a friend was telling me about problems with her boyfriend, I responded by making general statements about how “people” are and how they act in certain situations, but I never related it to anything that was personal to myself.

    And I do that all the time, with any topic. I’m way too guarded and never share anything personal, and I think the reason for that might be that I’m so ashamed of who I am to my very core, to the point that I can’t let anybody know anything about me or how I feel. So I basically have two modes when talking to others: comedian mode, or therapist mode. In comedian mode, I’m trying to make the other person laugh and I’m trying to be entertaining, offering funny commentary to what they’re saying or telling a funny story myself. In therapist mode, if the other person is sharing something personal, I acknowledge their feelings and validate them by speaking in general about “people”, but never about myself.

    Interacting like this generally makes you into a great listener, but won’t make you establish any deep bonds with people. Because if you never share anything personal, people feel like they don’t truly know you and that maybe you may not even want to deepen the relationship. This turned into a bit of a personal rant, but hopefully it can help you figure yourself out. As with anything, you gotta analyze the behavior and realize why this is happening; for me, it is a lack of sharing on my part, and the reason for that is a deeply rooted hate and shame for who I am. Now, of course, unpacking *that* is a much lengthier process. Hopefully some of this can resonate with you and be a starting point for your own process.

  6. Same, but for a sorta different reason 😅 and I’m probably the asshole for it.

    Ever since going to college and being away from my one childhood friend, straining that relationship, then that one ending, I can’t seem to make lasting connections unless it’s a bf/gf (til they lose my trust… I still love/care for them, but don’t want them in my life). I struggle to want people in my life more. Like… the drives are just too far to see people all the time (1h+) or I feel like my other friend took my former best friends side so we just don’t talk as much. I have my family, but I can’t talk to them like I can a friend (I can’t take sexuality or anxiety problems to any of my 4 conservative parents). None of it feels worth it any more. I’m probably the asshole, cause it’s not worth my energy any more.

    I can make plenty of work friendships and make a work fam, but seeing them outside of that setting… I feel like we’d have nothing in common, so I can’t get on board with outings or brunches or anything like that.

    I guess what I’m tryna say is I feel ya

  7. It’s great that you have small talk and having conversations down. That’s a huge head start honestly. Sometimes it can take time to find the people that you connect with on a personal level.

    Try and ask questions and be a good listener. Also when someone tells you something you can of course say “that’s nice” or “oh really!?” But also repeat a particular thing they said here and there.

    Example: someone says “my family went to myrtle beach not too long ago” it’s great to say “nice” or “that’s cool” but say something like “oh myrtle beach?” Or “myrtle beach is nice, how long ago?” it shows that you are indeed invested in the convo since you’re actually repeating words that they just said and in return the person you’re talking to will possibly show an investment in you as well.

    This could help you guys connect more personally. This goes for women and friends. Overall be natural, keep a positive mindset (that’s key), keep faith that you’ll find those right people 🙂 it’s just a matter of when 😀

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