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The Benefits of Sexually Trying people on as a Single Mature Woman

Updated on February 3, 2020
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Amy is an avid writer and a travel junkie and lifelong expat. She writes on topics from literature, to dating to sex. She has an MA in Eng.

Dating is Hard.

Let's face it. Dating is hard; and it only gets harder the older you get. Sometimes the fear of being alone drives us to make hasty decisions in dating and in partners. When I was in my late teens and early 20's I had barely dated and worried (as I watched all my friends date and enter long term relationships) that I would never get to experience it. So, at 21 when someone, whom I barely knew, asked me to marry him I said yes. Three years later the marriage was over, and I had to face dating again. I don't think we get wiser about dating and partners until we are at least in our 30's. When we are younger we set our own criteria of what we must have. Those criterion can range from the practical to the ridiculous. I remember my criteria in my 20's was long and exhaustive and so were my dating experiences. I've learned quite a bit in the 20 years since then and I'd like to share what I have learned.

"...with the advent of the mega digital age, it has morphed into this confusing triathlon.."

Dating in the Digital Age

Sure dates can tell you a lot about a person if the person you are out with is open, candid, and comfortable being themselves, but how often does that happen? Rarely. I found that people on are dates are often some amalgam of what they think the person they are on a date with wants to see. This does not mean if you are comfortable with who you are, you show up in your worst t-shirt and painting jeans and say "take me at my worst' and yes, I am looking at you men. You should still put an effort into looking your best since first impressions apply here and frankly it just shows respect. Dating should be a not so serious thing where you meet various people and see if there is an attraction and if you could like each other, but with the advent of the mega digital age, it has morphed into this confusing triathlon of weird characters, dick pics, and mixed messages. Hence, my most recent and enlightening experiment.


"I thought I could try different people on and see what I like and don't like."

Trying People on...

Last summer, I was living abroad (long term) and had gotten fed up with celibacy but I really couldn't be arsed with the whole dating bit. I decided, as I was scrolling through dating app options, if you can't beat'em join'em and so I joined Tinder. I put up the max number of pics, all face front and current. I decided that I was going to seek a friends with benefits situation, because why not? I thought I could try different people on and see what I like and don't like. What I got was a lot more (in the way of research) than I imagined.

Sexual Experimenting

I began my journey to vanquish my celibacy by matching with several men. Many wanted just hookups and at first I declined. I wanted someone regular I could at least get to know, not date but get to know. I soon realized I was open to both because both arrangements had something to teach me. As someone who has not dated a whole lot or had a slew of sexual partners throughout their life this was exciting and heady. I could just say yes, and they would come. It felt like that quote from Field of Dreams where the ghost tells him "If you build it, they will come". I posted, matched, said yes and they came. Ladies, I cannot stress this enough, if you decide to go this route, do it on your turf and your terms. I met many nice, respectful men who had no issue with this and the ones that did, had extreme reactions to my request and frankly scared me. I requested they meet me at a local wine bar near my place and if I felt comfortable with them and thought we'd be a good match, we finished our wine and went upstairs. The key to this, do not imagine anything more than what it is, two adults enjoying each other's company. Do not get wrapped up in it or get emotionally attached. It's sex, not a commitment. What I learned is that for most people it is difficult to hide their true selves during sex. We are at our most vulnerable during those intimate moments, even it is JUST SEX. You get a glimpse, several glimpses if you are really paying attention, into who they are. If they won't look at you, pay attention to that. If they tell you their life story afterwards, pay attention to that. What kind of lover are they? Are they in and out of bed quickly? Are they slow and sensual? Do they use your name? A man who won't look at you, is probably hiding something or is paranoid you or they will get attached. The only exception is if they are on the spectrum. If they're a hit it and leave type, they're likely selfish or extremely inexperienced. If they're slow and sensual and take time to see to your needs, well, then that's a good thing, but be careful, some players are really good at that. Which leads me to the last one. If they never use or almost never use your name, run as fast as you can, they are players and have no idea which of their toys they're talking to.

While these types of things don't matter for the one night stands and friends with benefits situations, they can help us when we decide to date so we should look for those clues.

I had some great experiences with my 'dates' and learned a lot. I also learned that society puts a lot of taboo on women taking control of their sexual lives and that even our vocabulary is shaped around making it not okay to do so. Women are sluts but men are studs. I am here to say it is absolutely not true. You can have a healthy sex life as a mature woman and date around as much as a man and there is nothing wrong with it. Respect goes both ways. Even in my experiences, I required a level of respect from the men I met and they took no issue with it. Go out, enjoy it, and learn from each experience.

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This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2020 alstocker

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