(This post totally rambles because I have, yet again, had too much coffee.)
Asking people out is scary. It just is. I have had people tell me it should be no scarier than going on an audition or a job interview. But that's clearly not true. At an audition you at least know they are looking for something and we all accept that if you go a job interview you are looking for a job. Saying "I would like to work at your company because I want to pay rent and eat" is different than saying "I would like to date you because you make my heart skip."
Asking someone out on a date is a whole other thing. I suppose if it a random person in a bar (something I haven't/won't/can't do) than it carries a lot less weight. "Hey, I know nothing about you but I find you at least interesting." Rejection just means, "I don't know you and I see nothing yet to find you interesting" or "I'm already involved." Even if it is "You disgust me," it has little weight because you don't know the person so you gives a rats ass. Bim bam boom done.
But I never ask just random people out. I ask friends out. Here you're in a very different place. You've gotten to know the person and they have gotten to know you. Maybe not super well but enough. Suddenly you are opening yourself up. "I've gotten to know you and want to spend more time with you and want to slowly wake up next to you on a Sunday morning." Rejection means "I've gotten to know you and, well, I've seen enough to know that I don't want to wake up next to you on a Sunday morning. But, hey, we can go see a movie."
I suppose this is the reason to not to try dating friends.
Over and over I have thought that junior high has a great system for the whole cupid-thing. We used intermediaries to get the message out there. "Besty Ann likes you" note passed in the back row of Social Studies. So simple and easy.
Okay, okay. I understand there is nothing attractive about being cowardly. What woman wants to date a man you can't even get the balls to say, "I would love to take you to dinner." (And I would argue that it is silly for men to find it attractive of a woman who does crap all to make her feelings knows but that's just me.) But as soon as you ask a friend out, you tweak the relationship. Either the friendship is new and light and you have suddenly put weight on it because they now feel uncomfortable about spending time with you, or the friendship is a close on and you have torqued it for the foreseeable future.
And perhaps that is the thing that has tweaked me on this in the past. I value my friend and working relationships too closely to tweak on a whim. By the time I get to the point that I want to ask someone out, I've gone through a fairly long process on it. I start to analyze their every interaction looking for signs they feel the same. (I don't want to ask someone out and have them say, "That never occurred to me. Um, sure. Impress me.") Yes, I build them up. I start to think "Fuck they are so out of my league" (again not an attractive thought) and need a crap load of positive evidence that they are interested. Less because I don't want to face rejection (which is there) but because (1) I don't want to make them uncomfortable around me and (2) I don't want to be placed in a pile of "boys who have asked me out."
However, I agree that everyone (boys and girls) should just suck it up and ask.
Anywhozits, if you are a woman and want a boy to ask you out because you don't want to face the chance of rejection yourself, here are my tips.
• Many boys are stupid and clueless. Don't be surprised if they don't pick up on subtle clues.
• Find ways of being around them. This isn't stalking (unless you show up at their homes or work). Just be around so they (1) think "Hey, she had no reason to be here except to see me" and (2) gives them an opportunity to ask you out.
• Don't play hard to get. Seriously. I know of no guy who find it attractive to be ignored. No, it's not cute. If you are both at a party and you make sure you never talk to him, that just says you don't care.
• Eye contact and touching. This is the biggest cliché but so so true. Looking n their eyes and lightly touching an arm may seem silly and cheesy, but it works wonders.
• Treat them different. The amount of women who have said to me, "I can't understand why he isn't getting the hint! I've been flirting with him all night," only to receive my response, "You flirt with everyone!" astounds me. Don't get me wrong. There is nothing wrong with flirting or being a flirt. Just realize that if you normal "joke" flirt with your friends, it is going to take something special to get your point across to that special person. Try extreme listening. Try flirting with out dismissing it with laughter at the end.
• Don't complain about not being asked out if you never ask them out. I put this up with people who complain about politicians but don't vote.
• Don't listen to me. Really. I have a horrible record on this account. My relationships I have all had more to do with luck and good timing and booze than any effort on my part. I have zero perspective on how I am viewed by the opposite sex. I am always in shock when someone finds me attractive. At best I view myself as Lloyd Dobler (as do 80% of the boys in my age group). Remember everyone thinks Lloyd is great but no one seems to view him as dating material for themselves. He ends up with he girl who hasn't dated anyone.
(Note: I have never known anyone named Betsy Ann. Mine was Michelle.)
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