Why I’m still single, according to my sister

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My sister and I don’t have the most typical or classic relationship, but one thing that she’ll always talk to me about is my dating life. She can be critical and over-realistic (I’m not the most realistic person and often say stuff like, “Reality has no place in my life!”) but her words are always appreciated at most, and at least, they make me laugh.

“What did you wear?” is always her first question, post-date. My sister is convinced that my wardrobe is holding me back from finding a fulfilling partner. Last night I went on a date and told her what I wore – a grey tank top, a cheetah print maxi skirt, and sandals. “That sounds relatively normal. Nothing high waisted,” she texts back. Actually, the maxi skirt was high waisted, I tell her. She’s immediately skeptical. My sister is sure that the fact that some of my clothes are high waisted – among all the other weird oddities that exist in my closet – is the reason that I’m still single & only attract people who are bad for me.

“Did he pay?” is always her follow up question. This one is so important to her. We have to pay to get our nails done and buy a new outfit for a date, she reasons. We also have to do our hair and makeup. I have never bought a new outfit specifically for a date (especially not a first one!) and I’ve never gotten my nails done, for anything. This is why you’re still single, she tells me. I’ve pretty much quit doing my hair and makeup specifically for dates, too, but I don’t bother telling her that. It’ll just put her over the edge.

I’m that girl who sometimes splits the bill on the first date – and other dates, too. I’m not really a believer in letting guys pay for everything. But sometimes I let them. Mostly out of laziness, or because they seem like they make more money than I do. (That non-profit career really doesn’t rake in the dough.) But, I’m used to being in relationships where I make more money, so I’m used to paying for dates myself. It’s never bugged me. My last boyfriend would pay maybe 10% of the time, but it was always special when he did. It’s never bothered me to pay for myself, or for both. But, according to my sister, this is just another reason why I’m still single.

Our conversations usually go on from there, based on where I met the guy or what we did. Often times she’ll ask questions like, “You got in a car with someone you met online?” If we’ve been dating for a while, she’ll wonder why we’re not committed to each other yet, or why I’m fine dating a couple of different guys at once (“You’re just kind of riding the wave, huh?”). Now and then she’ll ask questions about my sex life and express sheer horror or pity at my answers. I can just see her sitting there shaking her head in disgust at every answer I give her to any of her questions. According to her, I’m still single because I don’t put enough effort into the shallow parts of dating. Really though, I’m just not interested in dating someone who isn’t okay with the clothes I wear, or who loses confidence if the woman pays for herself. If a guy gets annoyed that my nails are unpainted, or I’m not wearing enough makeup, or my hair is a little frizzy or limp, then clearly he’s not the one for me. As much as my sister’s questions amuse me, they spotlight the dynamics of our own personal, very contrary values.

Here’s hoping the next guy doesn’t mind if my shorts goes up to my waist, or if I want to pay for my own cocktail!

7 thoughts on “Why I’m still single, according to my sister

  1. Amen to that. Life’s too short to worry about being perfect for someone you might end up trusting to see you at your worst

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  2. Hey Chloe, I see you still haven’t found your “Ross” but just like in the show, it may take you a whole decade too, to find the correct person – I wouldn’t say the “perfect” one because nobody is, nobody should be or try to – and you know what? 😕 That’s great, it’s a huge decision and taking years to decide sounds to me like a wise decision, not something to rush about. People always like to say: “well, I ain’t getting any younger”, but really, who is? Nobody! Even new born babies are getting older 😜, I just turned 27 last month and I feel like I’m 50.
    It’s funny because I have a problem with your sister’s complaints; I usually don’t like when girls try to dress or mask themselves way too much – especially when they dye their hair – or like the nails as your said, I don’t mind all that either but, if I like someone (boy or girl) I already find them attractive, they shouldn’t change anything at all, and if they are comfortable with being themselves, that’s more attractive, I feel all that hair coloring and tanning and excessive make up is a sign of a lack of self-love. And if my date feels comfortable in what is wearing, I think we can have more fun, one thing less to worry about. Is more important to me being healthy and having good hygiene than wearing something new and being all dolled up.
    And also, I hate when certain women would start to talk about gender equality but still expect to get paid for everything.
    I haven’t thought a lot about marriage, but I’m a very simple and practical guy when it comes to these things, I rather have a good woman for the rest of my life than having to juggle various relationships (at least partially 🙈 contrary to what a lot of people imagine about someone with bi tendencies), I guess that’s why cheating always sounded to me like a lot of unnecessary work 😒.
    Good to see you “back in the saddle”, recently you talked about Fitzgerald, and it so happens, unfortunately so, that a friend of mine passed away last week from an illness , he was in his 80s and didn’t had – almost – any family, so I cleared up and cleaned his place, he was a teacher and lived surrounded by papers and such, he had boxes filled with books, one of those boxes only had the label “witty” and they were mostly classics like Metaphysics, Pride and Prejudice, Beyond good and evil, but also had works like essays from Garcia Marquez (one of my favorites growing up in Latin America) and there was also The Crack-up, I haven’t read it yet, the quote at the start about living with two opposite ideas at the same time, really caught my attention, I probably will read this by the end of the month.
    You keep on talking about your life around MN, there’s no better way to learn more about a place one finds interesting than to listen from someone who’s been living there his/her whole life, I’ll keep an eye open 😊 have a good week start.

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  3. Oh man, I know that first impressions are important, but I definitely wouldn’t want to date a guy that was THAT turned off by what I wore what is obviously a very normal (and cute sounding!) outfit that he couldn’t appreciate getting to know me. Your sister needs to realize there’s no rush and sometimes things just don’t work out 🙂 And it could be for the better! Good luck to you!

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    1. I feel like if a connection is meant to be, it will be! I’m not sure we truly get hung up on looks, unless we are shallow. Besides, I love wearing weirdo clothing so I definitely wouldn’t want someone who couldn’t handle that! I love my sister so much. Her outlook is amusing on so many levels. I just need to remind myself to be patient.

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