Part of the human experience is the constant effort to better one's self. If you're anything like I am, then you're somewhat dependent on the involvement of others in your own betterment. Not because we're completely incapable of doing it ourselves, but because we just need that final push to do something that we might otherwise not have the nerve to follow through on.
To be honest, the entirety of the dating scene is an exercise in abandoning your comfort zone. The first mission is to get over whatever self-conscious issues you might have and ask your prospective mate out. Or find the nerve to at least speak to them. This is much easier done when you've already got some shared experience in common, such as school or work, but remains nerve-racking never-the-less. Personally, I have incredible issues even speaking to women, so how I ever get a date is beyond me, but the initial meeting is nothing compared to the full-on experience of venturing out with someone you're interested in.
It's quite difficult, at least for me, to figure out what you're going to do during your initial dates with someone. I mean, it's really, really hard. I never want to repeat the same date with one woman that I've had with another, because that's not only creepy, but also somewhat disrespectful to your previous relationship. Also, you're never sure what the other person would be interested in doing. Naturally, you can't just go in without a plan, because then she looks at you like you're an idiot, and becomes convinced that you go through life without any clue as to where you're going. I imagine it's an incredible turn-off for her (or him). A related turn-off is when you're just flat-out unwilling to participate in whatever your date has set up for you.
Seeing as how painfully tiresome it is to find something to do in whatever town you're living in, I would never dream of refusing an activity that my date really wants to do. Of course, if your date wants to take you trolling for hookers at midnight so you can beat and murder them, chop them up, and later bury them in the woods, that's a deal-breaker. But you have to be willing to push yourself to do new things, as it won't only impress your date with your willingness to go along with their plans, but you'll probably manage to impress yourself with what you're able to do.
The scenario is this: your date has surprised you with a trip to a karaoke bar. They've also taken the liberty of signing the two of you up for a duet (hopefully Starland Vocal Band's "Afternoon Delight"). If you're fortunate enough to be like me, then you're a terrible singer, and have incredible difficulty with public speaking (in this case public singing). Your options are to either go through with the duet, or to refuse.
If you refuse, your date is going to put in a lot of effort in trying to convince you to just suck it up and get up on stage with them. When that doesn't work, your date is going to be insanely disappointed, all of the wind will be knocked out of their sails, and things are going to grow slowly more awkward. No matter how great you were before this occurrence, and however you try to make up for it afterwards, you're always going to be remembered as the one that killed the fun. On the other hand, if you're the person planning the date, try to avoid this situation by not setting up anything that could cause embarrassment for the person you're interested in, because, let's be honest, you will never be able to look at them again without seeing how uncomfortable you made them on the first night out.
If you're brave enough to follow through, then good for you! You're going to get up there, shrieking your heart out, while your date probably cracks up halfway through the song and breaks down into tears, wheezing on the floor of the stage trying to catch their breath (true story), but you're going to become her or his personal hero. Afterwards, your date will be very impressed that you were willing to put yourself out there despite your vocal-impairment, and it's going to give the two of you something to laugh about for a years to come. When people ask the two of you about your first date, you can say that she totally embarrassed you, and she will claim that you did the same to her, and then you'll elicit a hearty "d'awwww," from your captivated audience. Suddenly, even though you were nervous, and an undoubtedly terrible singer, you've become the fun-guy (or fun-girl) who's up for anything. For the date-planner, I ask only one thing: please don't mock your date's lack of ability. Just compliment their bravery, buy them a drink, and continue on showing them a good time.
If you're willing to let your date expand your horizons, you may discover a great deal of things that you never knew you would enjoy until you'd been forced into them. This new willingness for adventure will greatly aide you in finding new ventures with which you can expand the horizons of your future dates.
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