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What I Learned from My First Romantic Relationship at 27

May 20, 2016
Content warning: In this post I discuss my history with dating, mine and other’s ways of seeing fat bodies, and assumptions and beliefs I held and hold about dating. My narrative here implies relationships are heterosexual and monogamous, which is just the way I envision and have my personal romantic relationships. I know that romantic relationships can be structured and experienced in multiple ways, so I wanted to warn about my limited discussion here.


Most people have entered the dating world long before 27, and I suppose I had my few experiences talking to and “dating” a few people throughout my late teens and early twenties. It wasn’t until late into my 27th year, though, that I met someone that I actually dated, someone who I talked to every day, saw multiple times a week, and formed a relationship with.

Dating and romantic relationships have had a complicated history with me. They always felt like work, and the not enjoyable kind at that. When I was younger, most guys I met in person who I liked were also liked by plenty of other girls, and they often found someone else more attractive than me. The rare guy that did throw attention my way did so behind closed doors – or in the safety of the internet. I never had the experience when I was young of being pursued by someone publicly with others knowing that he liked me. To be honest, that situation really messed me up. It drove home a lot of messages about desirability that I fully blamed on my body, not considering other things that also likely affected the way I was treated or seen. Having relationships that were secretive or never actually amounted to anything kept me safe in some ways, because I didn’t act on much, but it also made me feel intense shame.

To be fair, I think a lot of it was my body. I didn’t meet many guys at 18 who were into bigger girls, again, at least in public. Body positive spaces didn’t exist in my world, and there was a lot of cultural pressure to date certain kinds of people and to value certain kinds of beauty. Not like now (not that all of that has changed). Now it’s much easier to meet interested men. I started online dating when I was a senior in high school. I met one guy, C., who I went on a date with and felt enamored by – he was much older than me – only to have him “friend” some of my friends he met on MySpace (oh—MySpace) and message them privately. I had a big complex about this. I felt that my friends were 100x prettier, more interesting, better flirters than me. It actually took a long time for me to think I had something worth offering someone. I don’t think this is a rare story for women, and it just so happens that it’s also my story.


(high school prom my junior year)

In college I also attempted online dating. I had a string of bad first dates, lost hope, went on a couple casual dates with a guy in my science class, was told I was “too northern” for him, so that ended. I really lost hope. In high school I thought that I would be engaged or in a serious relationship when I left college. I honestly had some idea in my head that this was the place that people met their husbands (can you tell I grew up in the South?). It was a little humbling to realize I made it not only all 4 years of high school without ever seriously dating someone, but also all 4 years of college.

After college I went straight into graduate school. I quit dating. I focused on my studies and on blogging. I started this blog only a couple months after beginning my program, and those two years were an inspiring moment in my life. I didn’t need dating—I felt really fulfilled and very busy. Once life calmed down a little, after graduating and entering the work world, I decided to start online dating again. I work in a female-centric department, all my friends are girls, and I mostly talk to women all day. The likelihood of meeting someone in person felt slim, so online I went again.


(in the prime of my blogging days)

Online dating has both changed and stayed the same. There are still a lot of weird messages and approaches, but I also found at 26/27 that the men who were messaging me mostly knew how to start a conversation. I still had a string of first dates, but the ones I went on weren’t horrible. In fact, some were enjoyable, just none that made me want a second date.

When I met M. online, I wasn’t sure that I wanted to meet him. He was 24, and I worried about him being younger than me. Once he found out that I was a writing teacher, he used overly formal language with me – super polite, but that also drew me to him. I liked that he wanted to impress me and that he was persistent but polite. It felt like I was “worth” chatting to and meeting.

When we met up, I was instantly attracted to him. He had a big smile, and he was easy to talk to. He seemed nervous, and I was too, so that was helpful. It was one of those dates that you’re a little sad when it had to end, which was a great sign. In the beginning, we had a lot of excitement about getting to know one another. After Christmas, it was a little harder to keep up that excitement. We had both experienced some disappointment of things not panning out the way we wanted, and financial struggles kept us to only visiting one another at home. We got into a rut. I tried to talk about that rut and wanting to move forward, and we did some things toward that, such as me meeting his friends. I was also sick. Anemia plus some other things. It moved into a “friendly” relationship, and eventually it came to us talking and deciding we were better off as friends. I think I waited all that time for a reason. I’m happy that the first person I dated like this was M. because he was thoughtful, and he was kind. He respected me, and I respected him. I figured out a lot about myself in the process of dating him, which I want to share here:

  1. I feared not knowing how to be in a relationship, and that fear wasn’t really needed. Having never been in a committed relationship before, I worried that I wouldn’t know how to be part of a relationship. I wasn’t used to talking to someone every day. I was very independent – most of my choices only have to involve Lola and myself. Would I be able to care about someone else? Would I be able to handle having someone as such a constant in my life? Would I be what they needed as a partner? Could I be supportive? Yes. Yes. Yes. I could! The thing is that when you really like someone, you want to talk to them often. You look forward to hearing from them. You’re honestly curious about their day. I worried it wouldn’t feel natural, but it did. I think in general it’s hard to tell what someone needs as support, even your friend, and as you become closer you just have to communicate to find out things. It doesn’t mean it’s perfect, but I know now that I can try my best to communicate issues and attempt to resolve them.
  1. I have a very specific way of thinking about my fat body. It’s rooted in a history of experience and years of reading fat activist and body positive work. I didn’t show up one day with this view—it’s been developed and it’s nuanced. A new person in my life isn’t going to understand this fully right away. They probably don’t have the same knowledge that I have in regards to fat activism. M. had experienced body positivity, but a lot of his frame of reference was body acceptance oriented rather than fat activist. A lot of it was from popular curvy models. Sometimes he would ask me questions that I thought were really off, and trying to explain it without coming off as insecure was hard. He didn’t know what would trigger me, and I had to think through those triggers and my responses. For example, early on he asked me how I got so fat. That probably sounds like a horrible question to ask for many women, but he knew the extent to which fatness was something I thought about and wrote about. I was put off by the question, so simply stated and so “cause” focused. It’s a weird question to be asked – how did your body come to be – when you’ve had 27 years in a body that’s complicated. I had learn how to navigate these moments when I thought he either asked a question that I found faulty in and of itself or talked about my body in ways I didn’t agree with (like assuming that people looked down on me, etc.). I think it also reveals a lot of assumptions people hold about fat people. Individually, I had to figure out which assumptions I could challenge of his and be okay with him having held that assumption in the past. People don’t exist in a vacuum. Anyone I date will have heard non-ending messages about fat people. This is something I know that I will have to navigate again, and I think I am capable of making good decisions about how to handle it.
  1. I am not used to physical touch. While I learned to receive touch fairly quickly, it was much harder for me to give touch than I thought. I felt like a young, inexperienced person, and sometimes my insecurities of doing something wrong kept me from touching him. And when I talk about this, I mean resting my hand on his leg or holding his arm. This is something I will continue to work on. Intimacy can be hard, and even these little signs of affection can feel like hurdles (and small successes!) if you’re not used to them.
  1. I have to date someone who is considerate of my space and what I need body-wise. I have definitely had numerous occasions where my body size or my abilities have shown to need accommodations and/ special considerations. I’m used to navigating this on my own, whether that’s getting the appropriate chair or kindly reminding someone that I cannot walk as fast as them. Because M. was very considerate about what I could or could not do, what I needed in a general situation, or at least not making me embarrassed about something (such as breathing hard after walking up a big hill at the zoo), I now know that this is something I need in my relationship. I do not want someone who makes me feel ashamed of these little differences, and it was reassuring to have someone else think through some of these things along with me. It makes a big difference to not have to constantly speak up for yourself, and instead have someone think a step ahead and make sure that this accommodation or body-thing didn’t become a “thing” interrupting our time together.
  1. I am attractive to someone. I knew this, but I’m not sure that I thought it was possible to meet someone where there was mutual attraction. I mostly had dated guys who didn’t have a preference for big women, and dating someone who did definitely changed the way he approached my physical appearance. I want to be with someone who is attracted to me as I look at that moment – not a thinner me.
  1. I am smart. I don’t fall into a bad process of needing a man’s attention for my worth. This was something my mom mentioned to me. She’s seen people before who don’t often date get completely caught up in someone that does give them attention. I think she had a little fear that my lack of experience would lead me to bad decisions or getting totally caught up in M. in an unhealthy way. Instead, my age and independence helped me better decide what was okay with me and what wasn’t. I never felt dependent on him, just affected by him. I knew when to end it because it naturally went there and was no longer the relationship we had wanted it to be.

I will go into the next relationship knowing that it does take work, but it is also really enjoyable. I felt a little sad going back to my world of 1, but I am hopeful that I will meet someone great in the future.


19 Comments leave one →
  1. Jacki permalink
    May 20, 2016 4:01 pm

    Great sharing that I believe will be helpful and affirming for your readers. I recognized myself in some statements. It is so good that you are able to see these emotions or needs or things that you require in a relationship early on and given that you haven’t had a whole lot of serious dating. I’m not sure that I’ve developed skills to maneuver thru the dating game. Although at this point I don’t have much interest in those kinds of relationships anymore, had I been more attuned to who I am (as you are), I think I would have enjoyed dating so much more. Thanks again for sharing your experiences.

  2. May 20, 2016 4:14 pm

    Great post here! Thanks for sharing!!!

  3. Heather Roebuck permalink
    May 20, 2016 6:28 pm

    Glad to see you post again. I enjoyed reading your experience and hope you continue writing. 🙂

  4. May 20, 2016 10:21 pm

    This was such an awesome read. I’m so glad that you felt comfortable sharing your new knowledge in such an intimate way.

    I have to give you a round of applause for staying smart and independent. Three years ago I ended a relationship with a partner of ten years, and getting back into dating after years of being comfortable in a relationship was very difficult. My confidence in myself was seriously shot down after my relationship ended and I didn’t feel like I had much to offer a partner. As such, when I got into another dating situation, I was so thrilled that SOMEBODY liked me that I lost myself in that relationship and it was really unhealthy. I’m so proud and happy for you that you managed to maintain your sense of self in that relationship. That’s a huge achievement.

  5. Elizabeth permalink
    May 21, 2016 2:40 am

    I was reading this while nodding my head and thinking, “I’ve been there, too. Wow.”
    Thank you for your honesty. Thank you for sharing.

  6. Mbalenhle permalink
    May 21, 2016 5:22 am

    Thank you Rebecca for such a great blog post! I am 20 years old and I would like to thank you for preparing me the road ahead of me. I also want someone who’ll accommodate me and yet love me in spite of my body, not of my plus sized body. I think also have a way of thinking about my body fat – and I don’t know if I’ll ever be ready if someone asks me a question about my body, so I think this is time that I learn how to react to certain questions I might be asked. I think this article will linger with me for years to come!

  7. May 21, 2016 5:32 pm

    This is the most emotionally evolved piece on dating I think I’ve ever read. I’m so excited for you and the way you used this as such a learning experience!
    And I loved this line: I never felt dependent on him, just affected by him.

  8. May 21, 2016 8:43 pm

    Great post! Loved reading it! You are a strong, independent woman and I actually look up to you (even if I am older than you). You’re independent and know yourself in ways I can’t even imagine. I’m happy you’ve taken away some great things from this relationship, even if it did end up not going the way you wanted. Will just make you that much more aware of your wants and needs in your next relationship! I’m glad you are posting again 🙂

  9. Denisa Dellinger permalink
    May 22, 2016 10:19 pm

    Great to see you post again! I have been missing you. Oh girl! you have touched on lots of things that we all have dealt with. Whether we are a small “fat” (size 12-14) or a large fat, we have all suffered from body image problems and men. I know nothing of the world of online dating because when I entered the dating world, that was not an option, maybe we entered a dating service or match maker service but that cost lots of money so most just met the guys at school or work or a club. Usually these don’t end well because you can be who you want to be onine and you can lie. But I am glad you met your friend and had a good experience. Each one helps you prepare for the next. I tell you, I have been “skinny” and I have been fat. It is a different world. It is like you belong to this secret club where you are accepted. You are seen as cute and pretty and desirable. And even though you think you still have some work to do, you are seen by men as desirable and datable. Skinny people just don’t understand why we are fat and why we allowed ourselves to become that way. It is seen as some sign of laziness and unself-control and discipline. You are seen as less that a person and discounted among the human race. Why can’t you just lose the weight? You aren’t healthy being that fat. You see the stereotypes in movies and tv. We are the ones laughed at and jeered at. We are the “best friends” of the really pretty girl.

    Some of us, like you, have said what the heck and told the world that this is who you are. If you decide to lose the extra weight, you will. but it is not up to others to decide, it is up to you to do it for yourself, not just for a man. And as your friend M. showed you, there are those out there who like you just the way you are. I have seen lots of fat girls with boyfriends and husbands. So it does happen. Don’t settle for anything less than the relationship you want and that you deserve. You are a very beautiful, vibrant young lady who has it “going on”! You have blazed the trail for many a girl with your blog and putting yourself out there. And we like it!!!! Don’t be a stranger.

  10. Sara permalink
    May 23, 2016 5:08 pm

    Thanks for the great post! I’ve missed reading your blog! I too had a very hard time dating, never dated in high school period, was always a 16-18 through high school. After hs, just got bigger, it’s hard finding a good guy. Many guys told me I was too big to date and others just wanted to be friends. I’ve since found a bf finally at age 30, whose great and accepts me for who I am and thinks I’m beautiful. We’re expecting our first child next month, when I was young, I always thought I’d be married with children by this age lol. I’m just getting a later start than most. I do still find it hard to not be so ‘protective’ about myself, letting all my guards down, because deep down I still think I’m going to be hurt.

  11. May 23, 2016 7:50 pm

    I’m so glad you were able to learn great things from this experience about who you are and what you want and need. I had some of the same pre-conceived notions before I actually started dating at 25. My husband and I are celebrating our 8th wedding anniversary and I still look back on my life before him (he was the first guy I started dating) and think about how much I have changed in leaps and bounds in that time. It is a great feeling to learn about yourself and know yourself and acknowledge your progress along the way.

  12. May 26, 2016 3:37 am

    This is one of the best post I have ever read about dating and being full figured. Thank you

  13. Amanda L. Briles permalink
    May 28, 2016 10:52 am

    I often forget you have a blog but I always love when I remember and have weeks or months of reading to catch up on! I was pleasantly surprised to see a picture of us in this one! Thank you for keeping this blog going, I really enjoy reading it 🙂

  14. May 30, 2016 6:09 pm

    This is a beautiful, thoughtful, wonderfully written post. You have grown so much as a person, and I’m so happy to see this ability to think through and consider your navigation of a romantic relationship. I’m thankful you met someone who was as kind and considerate as you yourself are. The relationship evolved into friendship, and the fact that it did had nothing to so with your size – it had to do with where you both were with your lives at that moment. I’m so glad that this resolution leaves you open and more prepared for whatever comes in your future.

  15. June 2, 2016 1:29 pm

    A beautiful post from a beautiful girl x

  16. June permalink
    July 3, 2016 8:03 pm

    I thoroughly enjoyed reading this post! You articulated so many thoughts that I have had over the years especially the fear of not knowing how to be in a relationship!. Just as you, I never dated in high school or college and haven’t been in a relationship as of yet and I will be 37 in just a few days. That’s crazy, right? I often feel that God is being really mean by not allowing me to experience a romantic relationship but I hope it simply means that he is taking his time by grooming a perfect man just for ME!

  17. October 14, 2016 6:46 am

    I just loved reading this!

  18. December 22, 2017 6:07 am

    Incredibly impressed with your candor. This 48 year old woman could not have expressed it better


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