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Getting Personal: “I Wasn’t Slutty in My Twenties… and I Regret It”

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The following essay is a guest post written by my friend, Emily Morris.

When I was 21, I moved to Berkeley, CA to be a nanny. I didn’t know anyone there except my friend and her husband, who were both in their early forties at the time. I had a car to use and weekends off, and I spent most of my time going to movies alone or driving around the city. I went on one date with a guy who worked at the bagel shop. He kind of looked like Dave Grohl. When he came to pick me up for our second date, I hid in my bathroom and didn’t go to the door. Looking back, I think I was having an anxiety attack. At the time, I just felt like I was very, very shy.

After I moved back from California to Boston (where I grew up), the next few years were not very eventful, relationship-wise. I spent a year and a half with a crush on a guy who barely knew I existed, following him and his band (of course he was in a band) around like a puppy dog. I moved and changed jobs and had my first apartment alone, and I never really made any terrible mistakes. I had a brief relationship that ended as fast as it started, and then I tried online dating.

I met three or four guys but always felt like the chemistry was too forced, and I didn’t pursue anything. And, of course, online dating can just be bizarre. Like the guy who told me he’d be the one “in the white jeans” and then, when we met, he said, “You ask me a question and then I’ll ask you one!” When it was his turn, he brilliantly asked: “What’s your favorite color?” The fuck? I couldn’t help but wonder if that was all that was out there. But I didn’t really give myself the chance to find out.

I’ve never been especially bold or outgoing. In high school, I was happy to stay home most nights and weekends, obsessively journaling (!!), watching “Party of Five,” and listening to loud music. I’m a classic introvert — I get exhausted by long conversations with strangers, cannot stand small talk, and need to regularly recharge my “batteries” in my own home. But I’ve also always loved going out, and I did it a lot in my twenties. I just never felt like I wanted to “put myself out there” and I don’t know exactly why. When I went out to bars, I hung out with my friends and chatted, drank, laughed and HAD FUN, but I never hooked up with a stranger, or had a one night stand or a walk of shame the next morning, and, looking back, I regret that.

When friends tell me stories of their twenties — about random silly hookups and making out with people they never talked to again, I feel a weird twinge of envy. I have some fun and crazy stories, but I wonder about all the other stories I don’t have. Of course, they could involve STDs and broken hearts and hurt feelings, but they also could have been awesome. Now I think back about times in crowded bars when guys would talk to me and I would feel overwhelmed or awkward (or I simply just wasn’t interested) and I wonder why I didn’t talk to more people I liked or found attractive. Maybe it was a fear of rejection, which can be a powerful thing, but now, on the eve of turning 38 (tomorrow!), I think, if someone rejects you, then they didn’t really deserve you in the first place. I also, annoyingly, see pictures of myself from this time and think I look pretty damn cute. I wish I had known that — or had more confidence in myself.

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(Me at 23, sitting at the bar, being cute and having no idea!)

I spent my late twenties crushing on a friend, making out with him, feeling weird about a fall-out we had because we were making out as friends, and then, by the time I turned 29, we were in a relationship. (And, btw, he was the drummer from the aforementioned band. Life is cyclical). Now, nine years later, we live together with our two dogs and one cat; I am fully happy and content with the way my life has rolled out so far. But I wish I could go back and tell myself to take more risks, be bold(!) and put myself out there. I can’t tell my younger self that, so I’ll tell you: if you’re afraid of risks, don’t be! Be afraid of missing out on the rewards you get when you take them. Tell that person you like that you have a crush on him or her! Ask that dude on a date! Maybe he’s just as nervous and scared as you. Maybe he’ll say no. But the world won’t end, I guarantee it. Risks are for taking, life is for living. Don’t sit still at the bar waiting for people to come to you. Get up and grab a cute stranger and go for it. If nothing else, you’ll have more stories to tell when you’re old.

emily brownhairEmily Morris is a lifelong New Englander who eats too much cheese and drinks too much coffee but regrets neither. She loves Mark Ruffalo, Scottish accents, and the beach. She hates turtlenecks, the Kardashians, and her neighbor with the leaf blower. She is a currently a nanny, but her 2014 resolution is to do more writing. She lives with her drummer boyfriend, two dogs, and one cat in Boston. You can find her wasting time live-tweeting award shows on Twitter.

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Comments on this entry are closed.

Kate B. Kate B. July 15, 2014, 1:33 pm

All I have to say is me too and I hope it’s not too late.

avatar Christy July 15, 2014, 1:37 pm

Girl, I feel ya. I didn’t date until after college, and other than a month of semi-dating one girl, and around 5 online dates, I’ve only ever been in my current relationship. And I think I could have enjoyed a casual dating/hookup phase. Gf and I have talked about it, and basically, the door’s not entirely closed on the idea of a semi-open relationship one day. And that’s our compromise. But it’s not quite the same. I just tell myself that I’d take stability with her than crazy times without her.

thatswhat-she Meg July 15, 2014, 1:37 pm

I love this! I was the same way, but (thankfully, to me) finally had a couple years in there before I started dating my now-husband where I did start to take risks.

Ironically, it started with telling a friend of mine (who would have been terrible for me) that I had feelings for him. I flew to Chicago to visit him with this whole big plan in my head, but he (although he had been the one pursuing me years earlier) wasn’t feeling it for a few reasons. While I’m happy for obvious reasons that it didn’t work out, the act of putting myself out there- and finding out that even if the worst happened, it wasn’t that bad- gave me the confidence to take some romantic risks.

Over the next year and a half or so, I dated lots of different kinds of guys, and even successfully pulled off one booty call– and then started dating my husband. I really think that brief period of risk-taking made me more ready to settle down. I knew what I wanted, and could articulate it as my needs changed.

avatar kerrycontrary July 15, 2014, 1:47 pm

Very interesting! I have to tell you, I WAS pretty slutty (blah! I hate that term. Can we just so promiscuous?) in my early 20s and I don’t regret it one bit! So anyone who’s afraid that sleeping around will leave you feeling worthless about yourself? Well, maybe it will and maybe it won’t. But it didn’t harm me psychologically one bit! I don’t feel empty. I wasn’t filling a void. I didn’t (and don’t) have daddy issues. I just liked sleeping with guys I was attracted to and having fun. All I got was some good sex and when the sex wasn’t interesting, well at least the story about the sex was. And I never got an STD! Sure there were some awkward and embarrassing situations, but they were over as quick as they started. Basically what I’m trying to say is that I’m a big supporter of sleeping around. And now that I’m going to be sleeping with 1 guy for the rest of my life, I’m not wandering what else is out there.

JK JK July 15, 2014, 1:56 pm

I was far from promiscuous when single, and I have never wondered what else is out there.I don´t think there is a on size its all optio he (llkethere isnt in most things in ife)

JK JK July 15, 2014, 2:12 pm

Ugh typos. My keyboard is being stupid.

avatar tbrucemom July 16, 2014, 8:02 am

I agree. I also think there’s a difference between being curious, checking out what’s available so you know what you like, etc. and being slutty, or promiscuous, or whatever you want to call it. It’s great to have memories and to experience different things with different people, but a lot of women feel really shitty after one night stands. Not all relationships need to involve LOVE, but you should at least know someone enough to not have to worry about them being an ax murderer or giving you an STD (or worse).

Skyblossom Skyblossom July 16, 2014, 9:34 am

I’m like you. I was never promiscuous and have never missed it. I have never wondered what else is out there. I have never felt the desire to be wild. I think it’s a matter of knowing who you are and what works for yourself.

Dear Wendy Dear Wendy July 15, 2014, 2:09 pm

Emily, you were cute at 23, but you’re adorable at 38 (tomorrow!), too. Happy birthday, friend.

avatar Emily July 15, 2014, 3:12 pm

XOXO!!

Lyra Lyra July 15, 2014, 2:13 pm

I don’t get this at all. I’m a supporter of taking risks. I wish people including myself took more risks. But at the time in your 20’s, you didn’t want to sleep around or make out with random strangers or whatever and that’s totally fine. My intention is not to slut shame at all, to each their own. There is no one answer for everyone, but not everyone is “slutty” (I don’t like that term either) in college. Not everyone is ok with it. I sure as heck wasn’t and I have never felt the need to be…but you’ve changed as a person from your 20’s until now. You’ve grown, you have different interests and likes and wants and needs. You didn’t want to make out with the random stranger at 23. That’s ok.
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I remember in college we had a ton of programs that were sex positive and I can really appreciate that despite still being fairly conservative in that way. However as I look back I kind of wish that those programs had more of an emphasis on choice — choosing to not have sex is perfectly ok even when it seems everyone else is living their “slutty” college years. To each their own. One choice is not be the answer for everyone.

Addie Pray Addie Pray July 15, 2014, 2:24 pm

What’s not to get? I think it’s about how the author wasn’t slutty in her twenties… and she regrets it.

avatar lets_be_honest July 15, 2014, 2:29 pm

I assume she meant she doesn’t get feeling that way, not that she doesn’t understand what she just read.

Addie Pray Addie Pray July 15, 2014, 2:29 pm

or maybe you don’t get why she regrets it? i think with everything in life as we get older our perspectives change … I don’t think she means she wishes she had been slutty despite not wanting to at the time; she probably means she wishes she had wanted to be slutty. … I can relate. I kind of wish the same, too. I’ve realized sex isn’t that big a deal, but putting yourself out there, learning what you like and don’t like, not taking things too seriously, learning how to communicate with others, etc. etc. is a big deal, and i could have used more practice in all of that in my 20s.

Lyra Lyra July 15, 2014, 8:14 pm

I have my regrets, most definitely, but at the same time I wouldn’t be who I am today without those things happening to me you know? For example I regretted moving to North Dakota in 2012 to follow my ex, but without that I would have always wondered “what if?” We would have broken up either way but I needed that year by myself in a place all by myself to realize that I was worth more than what he gave me. My main point was that even though sometimes we wish we had done something differently, everything shapes us into who we are today. Our life experiences help us to learn and to grow. That was more my point. Looking back and wishing you (general you) had done something different doesn’t really benefit anyone. I wish I hadn’t wasted so much time regretting what I hadn’t done and spent more time focusing on what I can do in the here and now.

Lyra Lyra July 15, 2014, 2:33 pm

But at the time it sounds like she didn’t *want* to be “slutty”. She was 23 and NOT wanting to go make out with random dudes or sleep with random dudes. Now she wishes she had but who doesn’t have regrets?? That’s normal. I wish I had asked out the super cute dude in my college psychology class but I didn’t. Whatever. It’s in the past.

Addie Pray Addie Pray July 15, 2014, 2:38 pm

well, the essay works for a number of things – having lots of sex, i don’t think, is the only thing to glean. pretend it says, “i didn’t ask out the super cute dude in my college psychology class…. and i regret it.” but you’re right, no point in regretting the past. but then we’d lose out on insightful reflective essays that may resonate with others.

avatar jlyfsh July 15, 2014, 2:38 pm

I think that’s the whole point of the article. Ruminating on the past and offering a perspective to others. Not to be afraid to take risks. It’s not actually about being ‘slutty’. It’s about being willing to take risks in life. Whether that risks is sleeping with someone or taking a job that you’re scared of. And isn’t that what we all do when we comment on people’s letters in general. Offer advice based on thinking about our own experiences and pasts?

avatar Emily July 15, 2014, 2:54 pm

I just meant SLUTTY as a shorthand. I’m not really saying everyone should be a slut. Unless they want to. Then go crazy! Just be bold, was my point.

Addie Pray Addie Pray July 15, 2014, 3:02 pm

And I think you made that clear. I enjoyed – thanks for sharing!

avatar Emily July 15, 2014, 3:14 pm

Thank you!! Xoxo

avatar Tinywormhole July 15, 2014, 2:42 pm

I can’t help but feel like you really didn’t miss out on anything. Now, I understand wondering what experiences you could have had and wishing you had let loose a little more. But a couple of good points were made above: 1) that sleeping around can lead to feeling a number of different ways about it, and 2) your 23-year-old self didn’t want to make out with a random stranger, so you were being true to yourself at that age.

Your introverted personality sounds very similar to mine. The fact that you obsessively journaled when you were younger means you’re likely somewhat contemplative and tend to analyze what’s inside your mind. I can only say that for me (unlike kerrycontrary above), the sleeping around I did in my early 20s didn’t lead to good feelings. No, I didn’t have any horrible experiences or get any STDs, but I tended to rehash some of my more thoughtless experiences for awhile after they happened, and wished I could just erase some of those memories. For me, in hindsight, it didn’t feel great to sleep with someone and have them never call me again, even if it was what I had expected. I’m not sure I can explain why that is.

Now I’m in my 30s and married. I guess the only useful thing that came out my promiscuous 20s was learning how rare real chemistry is. But real chemistry is so good that I’m not sure I would’ve failed to recognize it had I not have had many other experiences to compare it to.

JK JK July 15, 2014, 2:44 pm

EXACTLY THIS
I know sex with my husband is AMAZING, even though I don´t have many points of comparison.

avatar Emily July 15, 2014, 2:56 pm

Yeah I’m not really sad about it. It’s just a thought I have sometimes. My boyfriend is cute as hell and I adore him.

Skyblossom Skyblossom July 16, 2014, 9:40 am

Exactly! When you have chemistry you know it and you don’t have to wonder if there is something better out three.

avatar dietcokeaddict July 15, 2014, 2:52 pm

I think everyone has regrets. I regret that I was hung up on my college boyfriend, partied too hard too often and that I did not take advantage of meeting new people or visiting the amazing city my college was near more often. But whenever I feel wistful about it, I remind myself that I might not be where I am now if things had been different. Since I am pretty happy with life as I know it at this point, I wouldn’t undo anything. :)

Skyblossom Skyblossom July 16, 2014, 9:43 am

I love this attitude! Our experiences shape all of us and we wouldn’t be who we are without them. There is nothing wrong with being a cautious introvert and a wild extrovert. They each have their own pluses and minuses and they each reflect a unique individual.

avatar Emily July 15, 2014, 2:52 pm

I am not advocating anyone should actually go out and sleep around if that’s not what they want to do. I just think there were definitely risks I wanted to take that I was too nervous or frightened to actually go for. I don’t regret how anything turned out but I do wonder what I missed out on by being scared.

I can’t actually reply to comments on my phone for some reason so hopefully people see this!

Thanks for the birthday wishes, Wendy!! Xoxo

avatar dietcokeaddict July 15, 2014, 3:01 pm

Maybe your reluctance was really some kind of supernatural force keeping you from something terrible happening.

Addie Pray Addie Pray July 15, 2014, 3:07 pm

Oh I’ve been thinking about that lately – like how close did I come to death (or meeting the man of my dreams, or meeting Tina Fey and becoming best friends forever) because something completely unrelated made me go right instead of left 3 hours earlier that day. … Or, like how if I had gone to brunch with my friends like I said I would, then call-me-hobo and i would not have been driving in a different area of town where I ran over a bunch of nails causing flat tires and missed meetups and lots of money …. Thanks, call-me-hobo, geez.

avatar dietcokeaddict July 15, 2014, 3:03 pm

Also, you’re being kind of bold now right? You had these thoughts and put them out there for discussion on a pretty public forum. That’s taking a risk right? ;)

avatar Emily July 15, 2014, 3:12 pm

Thanks that’s nice! Yeah I’m definitely not that worried what people think now. Which is one nice thing that happens as we age.

avatar jlyfsh July 15, 2014, 2:58 pm

This reminds me of the article Wendy posted the other day. I think about my early 20s sometimes and think about the choices I made and what would have happened if I had made more what seem like ‘exciting’ choices now. And those times when I wish that I had been willing to risk more. I’m thankful for the now too, but it’s definitely something that I sometimes think about when I hear about other people’s decisions!

avatar Holly July 15, 2014, 3:01 pm

I’m in my early/mid-20s and I’ve only slept with a single person that I wasn’t dating, and that person was a close friend/one time thing. It’s just not my thing *at all* – I like intimacy and snuggles and dates, and I feel like I really need to be close to someone to sleep with them. I’m also a classic introvert that prefers staying in, recharging, or going out but not being social with strangers. Will I regret that later? Maybe? I guess?

I think my issue is more that it feels like (perceived or in reality) a pressure to go out there, meet strangers and become instant-friends with them, and hook up with others semi-regularly. Like, by not doing those things, I’m living my life wrong.

Lyra Lyra July 15, 2014, 9:11 pm

Exactly this! I feel you Holly, I really do. The pressure to go out and be social and have “fun” really sucks. I hate bars. HATE them. I like smaller, intimate pubs, but I don’t see the need to go out to socialize together as one big group all the time. I would much rather sit on my deck drinking much cheaper booze with my friends than sit in a bar with 500 other people.

mylaray mylaray July 15, 2014, 3:22 pm

At first reading this, I was thinking “hell yeah” since I have had my fair share of casual sex, random strangers, sexual adventures, working as a stripper, etc. And it was fun.

To be clear, I don’t regret what I did. But there were certainly things I wish I did differently. I was too young and naive to always make healthy decisions regarding sex. I have a lot of “great” stories but there’s always the bad stories too. It’s no surprise my husband was quite the opposite and it’s something we both have a twinge of jealousy in each other. The fun part is comparing stories when I was 20 versus when he was 20.

avatar Lily in NYC July 15, 2014, 3:28 pm

I was sort of promiscuous in college and in my early 20s and regret it a lot. It was just so meaningless and I thought I was empowered by sleeping with whomever I fancied at the time. I look back and realize how hollow it really made me feel and that it was probably just a way to avoid real intimacy and being vulnerable with another person. I missed out on a few potentially great relationships with decent guys because I was too busy having sex with the hot charismatic dudes instead. It seemed like fun at the time, but I look back at these memories with regret, not nostalgia.

gigi gigi July 15, 2014, 3:41 pm

I was not slutty at all in college or my 20’s, because I was shy, introverted & most of all married. And like you I regretted missing out on that. However, just because you are past that age in your life doesn’t mean you can’t take risks or be slutty (ugh that word!) if you choose. When my husband left 4 years ago, I decided to find out what I had been missing. I am probably better equipped mentally to handle the situations I get myself into, & also much more social now. As well as the being older & just not caring as much what other people think.

avatar Smalls July 15, 2014, 3:53 pm

Emily, I feel like you and I would be good friends. I have literally had almost all of the same thoughts (and I’m a Bostonian!). This was a great, validating read – thank you!

avatar Emily July 15, 2014, 6:49 pm

Dude, let’s be friends!

findingtheearth findingtheearth July 15, 2014, 3:57 pm

I slept around in my 20s. Technically, I am still in them, but now that i have a kid, I don’t think it counts so much. I regret it sometimes, but not all the times. It’s a really weird place to be in. I am STD free, thanks to using protection. However, there is a lot of stigma attached to it, and I live in small town. I still get the “you used to be a slut!” feel from people sometimes.

Diablo Diablo July 15, 2014, 4:08 pm

I could have been sluttier in my 20s if I hadn’t been so clueless. I met M when i was 22, and she purt near had to rope and tie me for me to realize my opportunity. i look back now at signs i did not know how to read, and think “That woman was totally greenlighting me that time, but i didn’t realize it! Damn!” I now realize i developed all my “game” while i was with M, skills I now have but can no longer use. Can i still think of myself as slutty (a term I personally use as an honorific) if i seduce the same woman, like, 8 thousand times? But isn’t it natural for anyone to regret all the might have beens? I mean, in addition to all the ass i didn’t get, I now regret all the connections i failed to work, all the income i failed to make, all the drugs i failed to ingest, friends I failed to keep, steak dinners, sunsets, all the time I spent working instead of playing music, all the time I spent playing music instead of getting laid, etc. I’m not so obtuse that i don’t get Emily’s basically lighthearted point, but i also think that regret is a mindset, one that can consume some people. I try not to worry about what i didn’t do. I’ve got my hands full owning what I DID do. And (you guys knew this was coming, right?) I couldn’t really regret being in the right relationship from so early on, for so long, and with decades yet to come, could I?

avatar ktfran July 15, 2014, 4:35 pm

I’ve done quite a few great things in my life. I’ve also done quite a few shitty things. I honestly don’t regret a single thing. Could I have made a few better decisions, like be nicer to my sister? Sure, I know I could have. Did I probably hurt a few people? Most definitely. Could I have been more bold and tell that person I wanted to date him? Again, most definitely. The thing is, each time something good or bad happens I’ve learned something about myself, and how could I regret that? I truly don’t believe in regrets or what ifs, because I wouldn’t be the person I am today if those things didn’t happen. And I kind of like me.
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With that being said, I do occasionally wonder about past decisions and how my life could be different, but that’s all it really is, a wonder, or reflection if you will. But it’s never more than that. And I kind of get the same impression from this LW.
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And seriously, who really cares if you or someone else is or were slutty? That’s not directed to the LW at all.

avatar Portia July 15, 2014, 5:16 pm

Sometimes I wonder what if I’d taken more risks, pursued this guy or that one, tried drugs or went on a crazy road trip. But at the same time, I’m happy with the adventures I’ve been on and still go on. And who’s to say those people who tell crazy stories from their youth can’t have adventures now? I see the friends who tried their hardest to get their crazy behavior out in their youth and then settled down have again become restless.
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I fully intend on having fun and crazy stories from my 30’s as well.

Diablo Diablo July 15, 2014, 5:44 pm

And 40s, 50s and 60s, i hope!

avatar Portia July 15, 2014, 6:07 pm

You think I’d stop there? But I only look 10 years into the future at a time.

avatar Portia July 15, 2014, 6:09 pm

If I get to 70, I’m promising here and now that I’ll start dying my hair crazy colors. ;)

Diablo Diablo July 16, 2014, 11:54 am

I used to work in senior’s homes, and trust me, some of those people, now that their spouses are gone and death is truly imminent, have plenty of wild oats left to sow before their time comes, often at great medical risk to themselves. It ain’t over till it’s over.

avatar Emily July 15, 2014, 6:46 pm

Good!! Do it!

I’m not saying people can’t have crazy adventures now. I do it all the time. I am just saying start as soon as possible.

avatar Laura Hope July 15, 2014, 5:23 pm

Oh my gosh! If there was an award for the sluttiest girl in her 20’s I’d win. Hands down. Can’t even count. Best decade ever!

avatar Emily July 15, 2014, 6:47 pm

Haha good !