The Opposite Approach to Dating

I’m not a particularly outgoing person. I’ve always struggled with at least some degree of social anxiety. It’s gotten much more manageable as an adult, but one area where I still feel very socially unsure and awkward is in my dating life, and that’s why I have been trying to find other solutions like resources online, because when the angel number 2 is shared with you all your relationships improve and you can do better overall.

On a first date, I often find myself saying, “I’m sorry…I can be kind of shy until I get to know someone new.” I’m usually forced to say this after there’s been an unbearably awkward silence, or I’ve stumbled over answering a question, or I’ve gotten flustered and feel like I have to explain and justify it somehow.

I like to think my date will view my honesty and vulnerability as an attractive and endearing quality. However, if I end up having to say that line on a first date, there usually isn’t a second. Apparently, being honest about being awkward and shy is not endearing either. Instead of being frustrated about how unfair it is that shyness is such a turn off on a first date, I decided to try an experiment.

The Experiment: Stop being shy and start acting confident.

I decided to be like George Costanza in that episode of Seinfeld where he decides to do the opposite of everything he usually does when he dates someone. So, for my date last weekend, I did the opposite of what I usually do. Instead of wearing jeans, I put on a skirt. Instead of wearing little-to-no makeup, I used blush, eyeshadow, eyeliner, mascara, and lipstick. And instead of being quiet and flustered, I was talkative and confident. There are also sites that list lots of cool sex toys and choose the hottest so see there for some hot ideas.

When I got to the restaurant, I waltzed up to my date confidently with a smile and told him it was great to meet him. We sat down at a table and started having a nice conversation. I asked him questions, told him about my life and interests, smiled, maintained full eye contact, and used interested body language. I can’t say I pulled it off flawlessly, but I didn’t have to apologize for being shy. Even though we both decided a second date didn’t make sense, I felt good about the experience. I deemed the experiment a success.

However, the one thing I didn’t like about the experiment was how much it felt like an experiment. I’m so used to being endearingly awkward…okay, maybe that’s an oxymoron…but that’s how I see myself. I like that I’m a little shy, a little quirky, and a little awkward. That’s just who I am, and pretending to be otherwise felt kind of like lying. So maybe there’s a balance I haven’t found yet. Maybe I can be a little awkward, a little shy, and a little quirky while still being confident and talkative.

I guess that can be my next experiment: to not only act confident, but feel confident too. I’d like to figure out how not to run from or hide my quirks, but to embrace them so I can be myself and still make a good first impression.

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What are you like on first dates?

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10 replies to “The Opposite Approach to Dating”

  1. Kelvin Kao says:

    You know, this makes me wonder, because if there’s something I saw that I actually liked, I might actually consider using it as an excuse, “You know, then there must be a second date, so I can know more about the real you once you don’t feel shy anymore.”

    The biggest deal breaker is probably that there isn’t a conversation, a little bit of back and forth going on.

    1. Alana says:Author

      Thanks for the comment, Kelvin. I actually did once have a guy ask for a second date after I told him I wasn’t usually this shy. He said he wanted to see the real me. But I guess he still wasn’t that impressed with the real me, because he didn’t contact me for a third. Interesting perspective, though.

  2. I’m definitely an introvert, but I can “turn it on” when I have to – business functions, conferences, etc. It’s been a long time since I was in the dating pool – as in, before the Internet – but I did pretty much the same thing then. I also took up my company’s offer to send me to the Dale Carnegie Course, as I had to regularly interact with clients and give presentations. Best thing I ever did for my personal life! So if you can swing it, I’d absolutely recommend something like that. But there’s also the simple fact that the more you *act* confident, the more natural it will feel. Good luck!

    1. Alana says:Author

      Yeah, I should probably try to get more practice with public speaking and leadership. I’m sure that would help with my confidence too. Thanks!

  3. Emily says:

    ‘First Dates’ web series:
    Relevant to your interests?

    1. Alana says:Author


  4. Wow, I felt like you were describing me to a tee! O.o

    I am the most awkwardly non-endearing person when it comes to first dates! hahaha 🙂 Ah well, it was actually a comfort to know I’m not the only one whose felt that ways before!

    But as for your question…I would perhaps omit apologizing for “being shy, awkward.” I realized too late that that comes across as insecurity, which a level beyond shyness…and not cool. lol What I try to do now is that whenever I start feeling a “shyness attack” coming on, I focus on getting the other person to talk about his interests. And since apparently people enjoy talking about themselves, it usually works! 😉

    Good luck to both of us in the dating world! 🙂 🙂 🙂

    1. Alana says:Author

      I agree – I think apologizing for it ends up making things worse. Instead of being endearingly shy, I end up coming off as insecure and self-conscious. And yes, it’s always good to focus back on the person and ask them more questions. I’m often too nervous to think of any good ones, which is another problem.

      Thanks, I wish us both good luck too! 🙂

  5. Joel says:

    I used to be shy.

    Then I went to horribly awkward first dates.

    Now, first dates, are generally a bit more fun. I don’t mind shy so much. I’ve known enough introverts that I understand it pretty well.

    1. Alana says:Author

      Thanks for the comment, Joel! You go to the NaNoLA meetups in Pasadena sometimes, right? I believe we’ve met in passing. I appreciate you stopping by my site 🙂

      Experience definitely helps with the shyness and awkwardness. I like to think decent guys will understand my initial shyness and look past it, but some don’t, and that’s okay. It’s just part of who I am.

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