“Being forty, I wish I was living a life people envied. I’m not there and truly wish I was,” she began, as we settled into her living room couch to talk about her life in the first year of a new decade. She seemed to be alluding to her circumstances, the freedom that comes with being unmarried and childless. She cited Jennifer Lopez, a woman in her forties who is in fabulous shape, arguably looking better than ever, single and holding on to fame. “When I hit forty, I gained weight. It was like my womanly curves hit at forty.” She described a whole new crop of stress and change she’s begun to experience ever since her birthday–finding work and relationships draining, she naps (and she’s always hated naps); she’s at her highest weight with no motivation to make changes; she experienced her first bout of seasonal depression this winter; everything seems more expensive, creating barriers to the life she wants. And what life might that be?

She had believed from a young age on into adulthood that things would fall into her lap. “You just got married. Marriage and kids were your life path. You just did it.” She’d been raised by married parents who instilled the status quo of marriage and kids in her and her twin brother. She recalled that she hadn’t been taught anything explicit about love, about being in love or showing affection. No one said “I love you” within the family group. Physical affection between her and her parents ceased when she was about six years years old. Perhaps from the lack of demonstrated love, she became enamored of it, longing for a swept-off-her-feet feeling by a Prince Charming figure. “I had a fairy tale brain, and from a young age I really connected with the idea of romance.”

I wondered what her thirst for romantic love had looked like at that age. She told me the desire for a fairy tale love story began in earnest around the time she hit puberty. What did she do about it? She talked about an experience she had with a friend of her brother’s, a boy thirteen years old, like her. “He wanted to get physical. I felt like, ewww. I didn’t have boyfriends in junior high. I had crushes.” She described a boy in her class she’d not noticed until he moved away, causing her to fantasize about a goodbye scene involving a kiss, and-then-he-rode-off-into-the-sunset type scenario. She was an innocent, dreaming, not acting.

As long as I had known her, over a decade now, she had been a hopeless romantic, wishing for her Prince to carry her off, the dazzlingly charming man with whom she would live happily ever after. Was she getting that in her current relationship? No, and in fact one of the aspects that turns her off about her current boyfriend is that he does not perform romantic and thoughtful gestures. Those needs aren’t being met. How would someone meet her needs? “Women have a rule book, a playbook that is never given to men. Get to know me and you’ll figure the plays out.” I wondered why she wouldn’t communicate openly about her desires to a man in whom she was interested, including her current boyfriend. “Having to discuss the plays is a turnoff. Thoughtfulness is of critical importance.” Was there a man in her relationship history who got courtship right, was willing to search for the plays without being handed the book?

There had been a wonderful young man when she was twenty, whom she described as her best boyfriend. He was the first person with whom she had sex. I asked her to describe how he expressed his devotion. “He was great with sentimental gestures. One Valentines Day he got me flowers, heart-shaped cookies, and had taped my favorite movie, Bed of Roses. He had even covered the movie box in rose-printed paper.” Wow. “We broke up because I didn’t feel he was romantic enough. What did I want?!” she exclaimed, in seeming disbelief at her younger self. It turned out he was interested in marriage after a couple years of dating, and at twenty-two she wasn’t ready. She felt like a fifteen year-old.

She piqued my interest when she rolled her eyes and rather scoffed at what she called her “inner fifteen year-old”. Who’s that? She described that part of her as the “ultimate girly-girl”, enamored with matchy-matchy clothes, glitter, lipgloss, anything pink or purple. But beyond the material, the fifteen year-old seems to be an emotional state, a feeling of not being the boss or decision-maker, sometimes with little worry beyond the next day’s outfit. It sounded rather idyllic. But her experience of actually being fifteen hadn’t been anything like that. “I was a snappy little bitch. My brother called me Raging Bull.”

Nothing has happened the way she thought it would. She had believed that by forty she’d be married to her true love, and have kids. Sure, she’s fulfilled part of the career portion of her vision–a makeup artist running her own shop. As a young child she had envisioned she would one day be well-respected in her career, like the President. She had loved makeup from as early as she can remember, dreaming of being an elite artist. But even career hadn’t unfolded quite as expected, the petty dramas of retail management reducing the dream to a grind.

She was quick to add that she doesn’t have a bad life, it’s more that it’s all been harder and different than she expected. What exactly had she expected, and how had she come by those expectations?

“My parents said if I worked hard I could do anything. But they never showed me how.” So she put her nose to the grindstone, fully applying herself to any task or responsibility that came her way, including work and college. The pieces one fits together to make a life were obscured by the Big Picture. She was always waiting for something to happen as she worked diligently. “In college I expected ideas and a job to come. I felt everything was temporary.” But temporary became long stretches of years, as she waited for certain things to fall into her lap. A temporary job waitressing at Red Lobster lasted seven years. She’s worked at her current cosmetics company for more than a decade, though it brings little sense of fulfillment or interest. “I’m the last man standing. I’ve been around long enough to see everyone, including upper management turn over.” Her career experiences have ultimately led to the realization that nothing falls into one’s lap.

At times she’s used excessive purchasing to make herself feel better. “What I wanted from others, I was buying for myself.” What exactly did she mean by that? Shopping provided a chemical rush that made up for what was perceived to be lacking in her life. Having well-stocked makeup and accessories collections created a sense of security. Objects seemed to represent love. Not running out of items material felt like holding on to something she didn’t want to lose. “I bought my first pair of $200 jeans because a guy pissed me off. I thought, ‘fuck it, I deserve them’,” she recalled, of an early shopping episode. Somehow she never got into debt, helped by the fact she lived with her parents until she was twenty-eight, then with a boyfriend who supported her.

If nothing’s gone as planned, no Prince Charming or fulfilling jobs landing in her lap, shading her worldview from romantic to realistic, what does she want from the next half of her life? She saw the need for change on a trip to New York a few years ago. She had visited a psychic in her quest for how to change her life, seeking the lessons she didn’t receive growing up. The psychic told her she should practice asking for her needs. For someone who believes revealing the “playbook” cheapens the response, this was a radical idea. She’s come to understand she must be highly specific about what she wants, believing at once the Universe listens and provides, while at the same time “no one gives a shit about what you want”.

She talked animatedly about her ideas for the new year, with forty-one right around the corner. She plans to try something new each month, from horseback riding to hot yoga to pottery classes. “I want to find something new to love. I want to learn and expand my mind.” She finds that after years of an interpersonally-draining retail career she tends to cut herself off from people. She sees a need for a closer circle of girlfriends, especially given what’s lacking in her relationship with her boyfriend.

“Assuming the big picture will come together, years go by. I’m thinking on a smaller scale,” she told me of her current mental state. She’s seeking to gain a little fulfillment at a time, no longer clinging to a specific vision. She understands her inner sense of fear has grown over time, holding her back, and that she needs to work through it. “There’s no place for fear.”