Single woman
Credit: Jessica Durrant/Getty Images

I put the rim of an oversized red wine glass to my lips. I tilt it back to take a generous gulp of a Cabernet Sauvignon and listen to my date explain his aversion to fiction in a trendy neighborhood bar.

“Fiction is too creative,” he says.

As an imaginative, visual art-loving, mermaid-believing Pisces, I don’t know how else to respond besides, “Interesting.” Beyond his hatred of creativity, he also finds time to make some insulting comments regarding my affinity for Diet Coke.

I tell him, “Listen, I know it’s bad for me — but it is my one vice.” He shakes his head at me in disbelief.

As to avoid the awkward conversational pause and anymore Diet Coke shaming, I swiftly change the subject and conclude that this is not exactly a love connection. I continue with more small talk and plan to cut the date short once I finish my drink. While he carries on, my eyes wander subtly to my surroundings.

I start to imagine the life stories of the couples at adjacent tables. I wonder if anyone else is having a bad first date like me. The pair sitting to my left seems relaxed and full of smiles. Their level of comfort suggests they have been together for a while. I feel a swift, warm pang of jealousy in my gut and a familiar ache in my chest.

For my entire life, I have longed to reach a point in a relationship where I have that level of comfort and ease. I direct my attention back to my date and respond to his long-winded monologue about himself with a nod and a smile. After a second glass of wine and more forced conversation, I thank him for the evening and hug him before leaving the bar.

As I drive home, I remind myself to have hope and find some humor in the fact that I, a freelance writer, would match online with a man who doesn’t like fiction. This wasn’t the first bad date I’ve been on and I’m sure it won’t be the last, but it just feels like another night on the never-ending hamster wheel of dating. My emotions flow from frustration to sadness.

I feel completely baffled as to why it is so hard for me to connect with someone.

Credit: Wai/Getty Images

For as long as I can remember, I’ve been a romantic — ever since I was young and playing with Barbies. My Aladdin doll would always fall in love with whatever princess doll I liked most at the time. As I got older, I could recite the dialogue from any romantic comedy I could rent at Blockbuster. The fictional romances in classic books — Elizabeth Bennet and Mr. Darcy, Gatsby and Daisy, Catherine and Heathcliff — have fueled my desire for love since I first read them. With this knowledge base of timeless romances throughout the ages, I always thought love would happen in my life.

Since it hasn’t happened, the older I get, the more embarrassed I am to admit that I have never been in love.

Growing up, I went to a small school with less than 50 students in my graduating class. In high school, I had crushes, but those crushes would end up dating my friends because I was too shy to initiate anything beyond friendship. When I went to college, I lived in an all-girls dormitory and made the traditional bad dating decisions one makes in college. I longed for someone to care about me for a longer time period than the casual fling, but it never happened naturally.

Instead, I focused on being self-sufficient and having fun. In my early twenties, this meant I was always the fun single friend. I was happy with that on the surface, but in my mid-twenties, I saw my friends and roommates starting to pair off more seriously — moving out of my place and in with their fiancés and boyfriends. It just made me more aware of the fact that I didn’t have a partner in life. It also became harder to hide the realization that I wanted something more than a casual date or hookup.

With the number of my single friends dwindling, it prompted me to be less passive when it came to dating. I was tired of waiting for it to happen, so I actively joined dating apps seeking love.

Credit: bobmadbob/Getty Images

Turns out that searching for love through online dating only amplified my insecurities.

Apps increased my sadness over never having been in love, and worsened my fears that I never will be. Constantly going on dates created a constant cycle of putting myself out there, only to be rejected and missing that deeper connection. The process got me thinking about why I have been perpetually single.

I’ve had short-term relationships; most don’t last longer than a few months. I have friends who are serial monogamists — they were single for less than 24 hours before meeting someone new and starting another long-term relationship. Lately, I get ghosted after dating a guy for six weeks. I start to wonder, what makes me so different from them?

When I dive deep into my thoughts about never being in love, I realize that it feels a life milestone box left unchecked. An exclusive club that I’ve never been invited to.

Credit: Gary Waters/Getty Images

After dating unsuccessfully for a few years, the pep talks from friends who tell me, “It isn’t you — you just haven’t met the right guy” are beginning to feel repetitive. I love them for their unwavering support, but as I push 30, the fear of never having been in love only grows stronger inside of me.

Once I mentally reach that place of fear, I consciously take a step back.

It has taken me a while — but through self-affirmations and wonderfully supportive family and friends — I’ve reminded myself that being in love or in a relationship does not validate me as a person.

I have spent my entire life being a strong independent woman. I have searched for and found success in many other areas of my life. I cannot let this one fear consume me.


After the five-minute drive home from my neighborhood bar, I park in front of my house and make my way inside. I set my purse down, remove my uncomfortable heels, and plop down on my hand-me-down sofa. I search for a familiar happy movie to put on television and cuddle up with the fleece blanket for some relief from my dating woes.

I mindlessly watch the opening credits and recall a comforting thought: Although I am single and alone on the sofa, I ultimately do know what love is. My family and my friends love me. I also know how to give love. I am a loving friend, daughter, sister, and aunt. The truth is that no one knows how life is going to play out, what expectations will be met or missed. We don’t know who will come into our lives to help us learn and grow.

I just know that my life path has never been straight or uncomplicated — so I shouldn’t expect my dating life to be either…especially if I keep matching with men who insult my love of Diet Coke.