I recently decided to join the ranks of millions of midlife online daters and joined the world of Match.com.

I was more than a little excited (as well as somewhat nervous) about the prospect of finding someone to date (after more than a decade of self-imposed “I’m-busy-raising-my-son” dating hiatus). Before I could find my one true love though, I had to create my personal online profile. And because it’s been years since I really thought of myself in any objective way, describing myself in a manner that would 1) accurately represent who I really am, and 2) attract suitors, was no easy task.

On most online dating websites the profile consists of a series of practical questions, such as basic demographic information like age, marital status, education level, cultural background, religion and several questions that allow a narrative response where members get to expound on what their friends have told them about themselves.

So I poured myself a glass of wine, and settled in for what I thought was going to be about 5 or 10 minutes of tedium before I got to the juicy part—picking the man of my dreams.

I was relieved to see that I was going to be guided through this process with a set of pre-fab questions, most of which were pretty straightforward.

Eyes: Blue. Hair: Blonde. Have kids: Yes, Sometimes at Home. Faith: Spiritual, but not Religious (whatever that means). Smoke: No Way. Drink: Social Drinker (they didn’t have a ‘Drink Wine with Breakfast’ option).

The only question that I struggled with in the first section was body type.

On Match.com, you can choose from several options, but it’s very clear that only one or two are desirable: “Athletic and Toned” and “Slender.” The remaining options: “About Average,” “Curvy,” “A Few Extra Pounds,” “Big and Beautiful” and “Stocky,” I learned are all variations on the same theme: “Big as a House.”

Now, I don’t care if you hit the gym five or more days a week, at middle age, most of us in normal-land are “about average,” so, in a self-defeating attempt at full disclosure, I selected the “About Average” option in the drop down menu and moved on to the next question.

I quickly learned though, that in the world of online dating, saying your “About Average” is tantamount to saying,

“I’m a giant pile of blubber but if I wear Spanx and dazzle you with my personality, I’m just certain you won’t notice.”

So, I took the advice of some other online daters, and begrudgingly changed my body type to “Curvy” (this description doesn’t really indicate just where the curves are, or how many curves we’re talking about).

Then I got to the narrative questions, and my progress came to a stammering halt.

I was completely stumped by the first question: “Favorite hotspots.”

Huh? Hot spots? Did they mean something other than Trader Joe’s?

Since this question allowed for a narrative answer I typed the truth: “I’m not cool enough to have hot spots” and moved on.

Then, even more perplexing questions: “Interests and Favorite Things,” and “For Fun.” Apparently these questions are supposed to describe what the cool people do while at their hot spots. I sat and thought for about 10 minutes.

I consider myself a very interesting person. I really do. I am busy all the time.

Certainly I do something fun, but for the life of me I couldn’t think of a single thing, not one single hobby.

“What do I enjoy?” I asked myself (again and again).

Well, after a long day of hard work, I absolutely love to have a glass of wine, nestle into my couch and watch an episode of Real Housewives. I love to drink coffee in the morning, while reading Facebook and Twitter. I love to…ugh.

I’m a middle aged, about average-bodied watcher of junk television and consumer of social media.

I then cheated and looked at other women’s profiles and was brought to my knees. I mean, almost instantaneously my self-confidence came crashing down around me. My vision narrowed, I saw stars and thought I was going to pass out.

Apparently, there are women (my age) out there who are biking, hiking, camping, bungy jumping, rock climbing, water skiing, snow skiing, surfing (yes, surfing…in…the…ocean), and then in their down time, they’re jetting off to “hot spots”’ around the world on a moment’s notice. And if that wasn’t enough, they were doing all of this while wearing little black dresses.

I felt awful.

Don’t they work? Who has time for so many hobbies and interests amidst raising kids, working, paying bills, doing laundry and watching all of the Real Housewives shows?

Ultimately, I opted for sarcasm out of sheer frustration at having been shamed by Match.com, and for my “Interests and Favorite things” I wrote: bubble wrap, corrugated cardboard and bounce dryer sheets (I really do love all of these things).

“For Fun” I wrote: wine tasting (not a lie, I went twice in the late ‘80s), book clubs (I joined a Meet-up book club last fall and plan to attend the moment I find time to actually read one of the books), and concerts (I saw XTC at Madame Wongs, circa 1983).

Note to self: if you want to be a sought after date, get a hobby!

The narrative section of the online profile is where in 5000 words or less I was supposed to describe myself in some meaningful way that would set me apart from all of the other 1.5 million online daters in my age category and geographic region.

Again, I cheated and looked at the other profiles, and I learned a lot.

First, women are not just looking for a partner/boyfriend/husband—they are looking for a best friend.

Women also tend to want a man with a job, who isn’t a serial dater, liar or cheat. Most women are great communicators and almost all are eternal optimists (those “half-glass-full” types that we cynics find terribly unrealistic and a tad bit boring).

Men are for the most part also great communicators, and can’t possibly be working because they too engage in every sport under the sun. They are also optimistic and most want a woman who is “sensual” in a “my-wife-stopped-having-sex-with-me-years-ago” kind of way.

Most men also want drama-free women without any significant baggage (a desire no doubt borne out of their eternal optimism).

Oh, and everybody, (and I mean e-v-e-r-y-b-o-d-y), is an extroverted, entrepreneur, with a knee slapping, stage-worthy sense of humor, who loves being outdoors all the time (I’d like to note right here that I live in Chicago, and to profess a love of the outdoors all the time is a patent falsehood).

Despite my initial misgivings, I started crafting my narrative in much the same way,

”My friends tell me I’m funny, smart, considerate, forward-thinking, outgoing, optimistic, a great communicator and I love the outdoors.”

Ugh. Lies, lies, lies.

Well, on my good days, I am a very funny, smart, open, optimistic human being, who sometimes loves the outdoors (unless heat and insects are involved). But I’ve also been known to be an indoor-loving, backwards-staring, grass-is-greener, people-pleasing pessimist who communicates far too often through passive-aggressive kidding-on-the-square jabs, particularly when pissed off.

I can optimistically take the world by storm with my passion and zest for life, and I can also withdraw into a world of “why-me” pity when it seems abundantly clear to me that everyone has a better life than I do (which is completely and thoroughly unfair).

Ultimately, I settled on something that while presenting me in a generally positive light, was also authentic and truthful, while laced with a good dose of self-deprecating humor.

Has it worked?

I’d say for the most part yes, as I’ve received several emails from a range of men. Some of whom have expressed interest, and some of whom have just expressed appreciation for my honesty (apparently there are more “non-bungee-jumping-not-always-optimistic” people out there than I’d originally thought).

I haven’t been successful yet in finding the midlife man of my dreams, but I remain guardedly optimistic, in a glass-half-empty sort of way.

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Apprentice Editor: Brandie Smith/Editor: Catherine Monkman

Photos: Mike Licht/Flickr Creative Commons, Uncalno Tekno/Flickr Creative Commons