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I hypothesize that it will feel shitty to spend time on a nice note and to be ignored, but I don’t know, because I haven’t really tried.

I think it’s about time I try to understand my digital privilege. Emily Heist Moss is a New Englander in love with Chicago, where she works in a tech start-up.

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I believe exercising those empathy muscles is what helps us be better, kinder human beings, but it’s not fair of me to ask without trying to reciprocate.

There is plenty of privilege to go around, and while I spend a lot of time thinking about the big things I’m afforded due to my lucky draw, the little things I get are worth considering too.

Down the line, we can trade off and treat each other and enjoy the security in knowing there will be a “next time,” but for now, we both walked blindly into the same bar, so let’s walk out having equally invested in the last hour.

Why can’t I apply this “equal investment” attitude to the getting of dates and not just the paying for dates?

I write about gender on the Internet for crying out loud!

But every day, when I log into the dating site of my choice, I play the passive role, the receiver of attention, the awaiter of messages.

Finally, one of the cool girls writes back, and you will banter a bit, swapping favorite restaurants or concert venues.

You will ask her to meet up “in real life.” At the bar, you will chat nervously for an hour (she is not as pretty or as funny as you had hoped she’d be), and then you will be saddled with the check even though she ate most of the sweet potato fries.

I do not want my dating choices to be limited to the guys who are still optimistic enough to send a message; I might miss some good ones who are just tired of being ignored and I can’t blame them. I asked above why I should bother to get on the rollercoaster ride of being the asker instead of the askee, and I think the reason it’s worth trying is the reason it’s worth trying many things that make you uncomfortable; empathy.

Many times in my writing I ask men to try to understand how women feel out in the world, to take a walk in their shoes, to try on a different perspective to understand their own privilege.

She blogs every day about gender, media, politics and sex at Rosie Says, and has written for Jezebel, The Frisky, The Huffington Post and The Good Men Project. Emily Heist Moss is a New Englander in love with Chicago, where she works in a tech start-up.

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