The Stigma of Singledom and the Digital Dating Era

Readers, meet Bridget Borden. Bridget and I have been friends about as long as I’ve known my husband, Joe, and she’s joined the W&D Team as the director of events at Studio 125. Bridget left her corporate job to pursue her passion for designing and planning beautiful experiences, launching Bridget Borden Events in 2016. She’s graciously offered to write as a contributor, too! I’ve got to hand it to her for jumping in the deep end with her first post, with personal tales of navigating life as a successful singleton looking for love in the digital era. She has an incredibly big heart and I’m excited for you to get to know her.


Single at the ripe old age of thirty. When I was twenty-two, I never thought I would be in this position, let alone writing about it. And yet, here I am.

I’ve never opposed marriage or long-term relationships. My mother’s parents were married for seventy years, my father’s parents were married for over sixty years, and my parents are rolling into thirty-six years of marriage. My grandfathers treated my grandmothers like queens, and my father treats my mother the same way. So I could end this post, as well as my search for a mate, right now by blaming them for setting the bar way too high for any post-millennial dude that I find myself in a relationship with. I could, but I won’t.

Growing up surrounded by successful marriages certainly isn’t something to complain about – not to say these relationships were perfect, but all in all, my relationship role models have given me no reason to fear marriage. In fact, it was something I thought would just happen. After dating plenty of men – sometimes for a couple of weeks, sometimes for a serious length of time, I arrived at my thirties as a “singleton.”

Let me tell you, being single when you’re thirty poses a whole new set of challenges. To be single when you are twenty-two is empowering. It’s like having the confidence of Beyonce, the body of a Kardashian and the personality of a young Miley Cyrus – everything and everyone is seen through rose-colored glasses. For all that unabashed zest for life, I didn’t realize how liberating it was to have little to no expectations to “couple up.” You have time. No need to take dating too seriously.

Before you know it, being unattached went from liberating to all encompassing. Single when you’re thirty means vetting all first dates on marriage potential, acknowledging your aging uterus and cautiously approaching second dates because, let’s face it, that blind optimism in your twenties caused you to get hurt. And, truthfully, when dating becomes less of a hobby and more of a means to an end, it’s not as fun as it once was.

And while I’ve been changing, the dating world changed right along with me. Dating apps appeared out of nowhere – so to be a truly efficient dater in 2017, I had to learn to navigate the likes of Bumble and Tinder. One wonders what 15 communication channels does to the vulnerable psyche of those looking for love. When did flashing a look across a crowded bar or the casual group date become extinct? Now I have to take analytics into account. Freaking analytics. I’m assessing my success based on likes and swipes and notifications. I also found out saying “I’m new to this” on dating apps doesn’t exactly generate appropriate responses, if you know what I mean. However, I found one way to cheat the system: research. Diligent, thorough, research. I googled the shit out of these apps. I read articles. I combed through data. I asked Siri the following questions: What type of photos get you the most right swipes? What type of bio description shows that I’m serious, yet still fun? What are the best introduction lines to use on Bumble? (Bumble is where the ladies get the great privilege of approaching the guy first.)

My research started to provide a set of requirements that started to make online dating look less like a hobby and more like a full-time job, in which one may need to spend time and money to curate a profile that stands out. Here’s what my research revealed:

  • Three to four posed photos, in a natural setting (antithesis intended)
  • All images should showcase perfect balayage hair, paired with contoured makeup and great clothes
  • At least one photo of you traveling internationally, to prove you are adventurous
  • And, finally, a light, yet serious, description of yourself, focusing on your athleticism and extracurricular activities. Example: I include my Uber rating in my self-description

My experiences support my research.

After taking a step back, I concluded dating 2017 meant revamping your wardrobe, finding a photographer to essentially be my personal paparazzi for a day, booking a trip to Thailand purely for the photos and a membership at least two boutique gyms. All that effort and what do you get? Most of the time, a date with someone I’m halfway interested in, yet guilted myself into agreeing to go out with because of all the effort I put into getting the date.

You guys, I’m exhausted. And I know I’m not alone. Here is a little appetizer of what I experienced. Please tell me if you have, too.

  1. My first Bumble date, completely unsolicited, told me about the best places to pick up single moms.
  2. My second date texted me photos of juice sitting in the snow at 5:00 am (also unsolicited).
  3. I had high hopes for the fifth guy I went out with from Bumble – he was employed, had a car and health insurance (score!). We dated for a few months, and most of our conversations surrounded the three sailboats he owned. Frankly, I stuck around for the third month because I look good in nautical gear and thought sailing off into the summer sunsets sounded quite lovely. Fast forward to the end of that relationship and, spoiler alert – I never saw the sailboats, and he asked me to buy him a couch. Looking back, I’m relatively certain the sailboats didn’t exist, as a dear friend kindly pointed out the images he shared of the boats look a bit like stock photos. These are just my stories. Everyone in the office at our studio has at least one horror story to share, but for every tale of failure, there were ones of success. So, my success rate is low. Why do I keep trying?

Because I tell myself it is what I ‘should’ be doing. Almost daily basis, some measure of society says I’m doing something wrong just by being a single thirty-year-old. I often think I should have found someone to marry by now, and I should have a kid on the way. I should have a house in the suburbs. I should have more money in my savings account. As my beloved therapist says, I should all over myself, all the time.

When I take a step back from all the should-ing, the true answer of why I continue dating is because I want to spend my life with someone who enhances my life. Someone that makes me better in the areas of life I fall short. Someone that gives me energy when things get hard, someone that makes me laugh and smile. I constantly remind myself that I already live a very fulfilled life. I have a growing career with a business I’ve built from the ground up, I have an incredibly supportive family and the most amazing friends, who may, in fact, be my soulmates in life. Instead of looking for a boyfriend or husband just to say I have one, or to avoid the awkward looks and questions from people who can’t believe I’m single as they try to figure out what is wrong with me, I’m looking for a partner to share the great life I’ve built for myself. And I don’t plan on settling for anything less.

I am reminded that just because I’m approaching adulthood differently doesn’t mean it’s wrong. Remembering that choosing to solo binge watch Real Housewives on a Tuesday night, instead of meeting a Bumble date for a drink, is a choice I am consciously making. While much of life is out of our control, your existence is not forced upon you – consciously making decisions that are guided by what fulfills you is incredibly important to living a great life. If a partner enhances your life and that’s how you choose to feel fulfilled – that’s wonderful. If it’s your job, or your dog, or your closet, that’s great too. Understanding your self-worth, defining what success means to you and making fulfilling choices are more important than making decisions because you keep hearing the word should. It’s important to keep YOU in mind when crafting the perfect Bumble profile or to spend time with people you don’t want to. Focus on what makes you happy and don’t apologize for letting go of the things that don’t.

So, for those of you reading this that are in a similar position to me, I, unfortunately, don’t have slam dunk dating techniques – because let’s face it, if I did, I wouldn’t be writing this. I can only encourage you to live the life you want to live. And know I’m right there with you, consciously choosing to plug away on a dating app, or It’s Just Lunch or setups. I know can be rough out there. I see those same guys you do, posing next to deer carcasses in their profile pictures on Bumble. And for as long as we choose to continue on the dating path, enjoy the dinners, the drinks and the funny stories you can share with friends – because maybe it’s on date two or date eighteen – you’ll find yourself with that one perfect person and it will all make sense why you kept coming back for more, even if that person you found is yourself.

Worst case scenario, flip your profile over to Bumble BFF and make some great new friends to share a glass of vino with – win/win.

Graphic by Nicole C


wd_contributor_headshots2Bridget Borden is an event planner living in Minneapolis, MN.  At an event, you’ll find Bridget carrying a Mary Poppins bag full of ‘necessities’, talking on a walkie and making sure the linens were steamed.  Besides managing beautiful moments, Bridget loves watching sitcom reruns on Netflix, attempting to be a yogi, and is the one often laughing at the joke no one else thinks is funny.

  • Loved this line “Three to four posed photos, in a natural setting (antithesis intended)” hah!

    I think digital dating is hard because often people don’t know how to describe themselves! And not for a lack of words, but I think we don’t know what draws people to us as it’s the nuances in our personality/being that make us special and how do you describe that??

  • Oh god as an almost 30 year old fellow single lady ALL of this meant something and rang true…this in particular:
    “When I take a step back from all the should-ing, the true answer of why I continue dating is because I want to spend my life with someone who enhances my life. Someone that makes me better in the areas of life I fall short. Someone that gives me energy when things get hard, someone that makes me laugh and smile. I constantly remind myself that I already live a very fulfilled life”

    Thank you, it was just what I needed to read right now, even if I haven’t re-downloaded the apps just yet!

  • As a 31 year old and going through a divorce, I am terrified of getting back into the dating game. That being said, this essay has confirmed my decision and idea to focus on myself and be happyily fulfilled alone. I look forward to more of these, Bridget!

  • I appreciate you acknowledging your fulfilled life. I think that is sometimes overlooked when we are searching for companions. So by luck and proximity, I found my partner when I was very young. Eleven years later (we were only 24 when we hitched), we’re still happy as ever. I say that not to gloat, but to honor your commitment to finding a partner who enhances the great person you already are, independent of him/her. While I found love young, I find it excruciating making other meaningful connections (friends) now that I’m not in the effervescent space of college. In fact, I only keep in touch with 2 people from undergrad, while my solid high school group still jibes 15 years later! I was struck by how similar the journey for companionship (partner, friend, mentor) can be. Sometimes even after you find your someone, you still need other relationships to round you out. As a married couple we sometimes feel like we are ‘dating’ other couples and it can feel pretty forced and awkward. Identifying ‘enhancement’ isn’t always obvious.

  • obsessed with this. you couldn’t have said it any better. though I’m a couple years younger, I relate with every little thing. dating is just hard…but the free dinners and drinks are a total bonus!!! good luck out there ladies!

  • This is exactly what I needed to hear today, loved every single word of your article! I’m 29 and just a few months ago I ended a five year long relationship and to be completely honest, getting back into this crazy dating game sounds absolutely terrifying 🙂 Good luck to all of us out there!

  • i appreciate your honesty and vulnerability, but i’m so sick of hearing “how to get swipes on tinder” ! use pictures you already have, make your bio say something about you without saying it directly (mine is usually something sarcastic followed by “don’t be boring/send me memes”) and send messages to people you are actually interested in (if you find someone interesting it shouldn’t be hard to come up with a first message. when in doubt, test them! if their bio says “i love quirky people” say “how quirky”, it gives them a chance to share more about what they’re interested in and you can see if that appeals to you)

    remember that if you’re harkening back to the days when you got dates by making eye contact with a guy in a bar (i’m 22 so i have No Idea what that was like), you wouldn’t want every guy in the bar to be hitting on you, just the one you’re interested in! obviously if you tone it down to appeal to the masses you’ll get more swipes but you aren’t gonna find someone who gets you.

    i do love the reminder to devote time to yourself, and i only wish bumble bff were more widely used !

  • Loved this essay. As a 31 year old who has been single or only casually attached for much of the past decade, it really hit home for me. I do try to celebrate my singleness too–it is a gift, to be able to make my own choices and lead my own life, and I think that sometimes gets lost. I also want to recommend reading Rebecca Traister’s “All the Single Ladies” for affirmation of singledom. It’s a reminder of all the incredible and powerful things that independent and single women have done for the world and for themselves.

  • Thanks for your post! I love your attitude towards dating. I approached the whole online adventure similarly – with positivity. My goal was to meet someone, but also not to become jaded by the whole process. I even took a break from dating from age 34 – 35 because I didn’t want to lose myself in it, and wanted to develop other hobbies other than dating. I started again on Tinder at 35, just to get my feet wet. It was incredibly weird. When I looked at potential dates, I just tried to tell if they were a good person. Sometimes my instincts were good, and sometimes they weren’t. Mistakes were made. I met my husband on Tinder (The connection was not instant, but I’ve never expected that). I got married at 37. It’s possible!

  • Oh, I can relate and remember those days. I am actually getting married in a few months, but I’m 37 now… I was single until halfway through the year I turned 33, and (ridiculously) I’m marrying my college sweetheart that I met at age 19 and then took a 12 year break from dating him. I really found it very hard to forge connections with people I met through online dating (and I tried for so many years!) I think it just puts people in the wrong mindset. There’s always a veritable buffet of new possible dates available and it’s hard to decide to stop looking for something better. The non-committal attitude is hard to overcome. I eventually just gave up with online dating and figured I’d either find someone by chance in my real life, or I’d become a crazy dog lady.

    I guess it worked! (I think I became a crazy dog lady anyway though)

  • Thanks so much for your post I thought you managed to sum up the plight of many like you (and me). Its interesting how there is still such a stigma about being single closer to 30 (and beyond) and confronting this is refreshing and reassuring. I tend to find, irrelevant of the life goals you achieve, be it buying a house, a promotion, winning an award the greatest measure of a woman still seems to be whether or not she is in a relationship with a man. I often question whether anyone other than me will be happy that I am enough for me!

  • I found this post as patronizing as any other article about women who are dating over the age of 30, which are always written by a woman of course. I think the author is making a big mistake to assume that all single, thirty-year-old women are thinking about marriage potential and their “aging uterus” when they go out with a guy for the first time, or continue to date. Essentially focusing the article on meeting that “one perfect person” caused the story to fixate on the “stigma” of singledom – surely that’s what we are all trying to get away from as women? Articles like this just make matters worse, not better, for females.

  • Great read! I thoroughly enjoyed it.

    Bridget, if you see this, it seems the Instagram link on your website is actually linking to the WRONG Instagram account. I managed to find your actual Instagram account with a search, but it’s under a completely different username.