Times Square: 49 Years in the Making (Me That is)

Time to take photos.  Yay!

Nothing a 49 year-old woman enjoys more than immortalizing her aging body and face and sharing it with the world.  Not that I ever enjoyed having my photo taken. Like most of my gender, I’ve always struggled with self-image.  Since middle-school, maybe even before, I felt ugly and awkward and wasted decades tearing myself apart from the inside out, one dimple, one pimple at a time.

I recently finished recording new songs for an EP coming out soon, called “Firefly in a Jar.”  The last time I released a CD, I was a solid 15 years younger and frankly, when I had forgotten all that goes into “releasing” an album.  My existing photos were all supremely outdated, and don’t reflect what I look like now or the material on this new EP – at all.  So, when it came time to think about new photos for my album and website, I struggled with what direction I should take.  I consulted with PR queen, Beatrice Bugnosen of TheOutletmusic.com, who suggested I find someone I could feel comfortable with.  The words photograph and comfortable do not belong in the same sentence as far as I’m concerned!  Beatrice conjured up a bunch of key words to have in mind for the session, “nostalgic, warm, eclectic…” among many others.  Still I felt panic.  I don’t think of myself in terms of adjectives. “Busy,” how about that adjective!  The session was only a few days away…  First I needed a photographer.

My current job is Director of Communications for a large preschool.  Basically this means I email a lot of people and get involved on some level, in just about everything.  One dedicated parent graciously volunteered the services of her then nanny, who also happened to be an aspiring photographer, to help shoot various school events.  We took her up on that offer and I got to know the very talented, Samy Ruby. She photographed our preschoolers, skillfully, capturing their squirmy, adorable effervescence in still photos.

Since I spend most of my time at work, when thinking of photographers, Samy came to mind. I reached out to the parent who initially recommended her and was thrilled to learn that Samy was no longer a nanny and was in demand as a full-time, professional photographer.  After looking at her website, I understood why!  I remembered how generous she had been with her time and how easy she is to talk to and I confess that, after checking out her photos of Christina Perri I was blown away. Yes, THAT Christina Perri. We locked in the date; Columbus Day.

I dutifully forwarded Beatrice’s key words to Samy. Life continued on its habitually insane trajectory and I had absolutely zero time to dedicate to brainstorming the concept behind the photo shoot.  Then, A few days before Columbus Day, over lunch with the kids, my husband blurted out, “I think you should wear your grandmother’s slip and stand barefoot in Times Square.” He’s a visual artist and that was good enough for me.  I didn’t even ask why. I just said, sounds like a good idea – I’ll try it.  Maybe. Not like I had any other ideas!



My childhood memories of Times Square couldn’t be more different from the new Times Square my children will remember as the mecca of lights where we attend the New Victory Theater. I love this photo which shows a marquis, “A Holy Terror – Jennifer.” Hah! I believe this photo is from the early 1970s.

Samy and I spoke and  I mentioned the concept to her.  She was game.  We would also be shooting in my apartment and in Central Park (bien sur) and it would be an all-day affair.  This was all decided the day before!

The next day, Samy, the consummate pro, arrived with heavy gear and an assistant while the makeup artist (also pulled together in 24 hours) was still putting the final layers and touches on my “natural” face. We got to work and at each point, Samy made fun, guinea-pig-like giggling noises when she got a great shot.  I joked around a lot with Samy (early 20s) and her luminous assistant, Lluvia (also early 20s), about being older, trying to find flattering angles and other nonsense.



Times Square in 1966 the year I was born.


We ate lunch together and I discovered that they are both, in addition to being young and beautiful, bilingual, computer geniuses, semantics/linguistics maniacs and brilliant off the page.  When I was in my 20s I’m pretty sure I would have been intimidated and felt diminished by their incisive intelligence and effortless confidence. In my early 20s I feel like I was painfully lost and insecure.  As a 49 year old I could only feel immensely proud of these two exceptional women and honored to share their company.

The shoot continued and there were lots of giggles and more great shots than I can count and we were down to the final concept; The Times Square night shoot.

Samy and I said goodnight to Lluvia and we headed south on the crowded subway.  When we emerged at 42nd Street, Samy noted that the Times Square jumbotron wasn’t operating (jeezuz, I hadn’t even thought about that – dodged that bullet!).  We began scouting out a place where I could change clothes. Samy spotted the Olive Garden restaurant nearby (Why?  Seriously, why would you come to NYC to eat at the Olive Garden???).  I asked the hostess if I could please use their ladies room to change into a “dress.” I came out of my stall in my grandmother’s black slip, which in my mind looked like a dress.  A woman flattened herself against a bathroom stall and said “honey, don’t come out.”



As I primped in the mirror, I heard her say again, “Sweetie, stay in there, don’t come out yet.”  I looked at Samy who shrugged and turned to look at the woman who then barked at me, “That looks like a slip, and my son is in there.”

“It is a slip.” I responded nonchalantly and continued primping.  Her problem, not mine.  Bear in mind, as you can see in the photo, it touches my knees and reveals NOTHING!  I was wearing a bra and underwear neither visible through the opaque slip. What?!

Then, I had another thought.  Hey, I must stand out.  Cool!  I thought I just looked like another middle-aged overly-dressed tourist in a slip dress and high-heels, but apparently I looked like something a mother should protect her young son from viewing (albeit this lady was clearly deranged). Wow.  Me?  Really?

We hit the street and Samy started shooting.  She had a silly smile on her face as she dodged tourists gawking and pointing at us.  Mostly, they ignored me and swarmed around me as if I were just another of many obstacles.  I took a bunch of photos with my shoes on.  Some with my guitar.  Then shoes off.  NOW people began staring.

You know how I felt?  Fantastic!  This is what 49 feels like. I couldn’t care less what anyone thinks of me or if anyone is looking at me or NOT looking at me.  In that moment, I felt beautiful.  Powerful. Alive.  Happy.  Silly!  At one point, in this photo, a woman shouted at me, look out – as she pointed out a lit cigarette butt a few inches from my feet.  Sammy caught that moment in this shot.  I love it!  The good Samaritan looked about my age. Instead of her thinking I was a barefoot, freak in a slip to be avoided at all costs, this middle-aged bystander was looking out for me.  She kicked the butt to the curb and we continued.  Score one for the sisterhood.




When we were done Samy asked, “Doesn’t your face hurt? Mine hurts from smiling!”

I wasn’t worried about germs.  About onlookers.  I wasn’t thinking about whether or not I looked fat or tired.  I knew Samy would take the best shot possible and I would just be me and if I were lucky, it would all look good.

Because, 49 feels good.  This is the craziest time in my life.  Among other things, I have a full-time job, two kids, I care for an ailing dad while trying to keep one foot in music, and my life is full, full, full.  I’ve said before, Sandwich generation my ass – I’m a panini!  But when I think about it, and I do try to be mindful, I am so damn fortunate.  I have everything I need.

I have lived 49 incredibly full years.  At this age, you begin to internalize what a privilege that truly is. It is nothing to be taken for granted.  Each and every day is a gift. I have been blessed with more than 17,885 gifts and counting.


© 2018 Jenny Bruce