In mid-August I found myself getting double takes as I sat at an outdoor café table. It could have been the three feet of bare leg that was dangling, the bright white tee shirt atop my cutoffs, the rich red hair standing out at crazy angles, or the huge martini in one hand and a smoldering cigar at my lips. Hard to say.

How I started my day was working my List of “100 Things to Eat and Drink in San Diego” like it was my job. The list is from Alice Q. Foodie’s blog and it’s brilliant. Being new to San Diego I have been exploring neighborhoods on my stomach with her list in hand. The list was becoming soft like thin cotton gingham and food stained. There were notes from waiters, waitresses and bar keeps on the back of places they loved. Can you tell I love food, I am a foodie. I work out every day so I can eat all kinds of lovely things. So this day I was exploring downtown there were a half dozen places on my list and I planned to have a course, a cocktail, just the item she recommended at each establishment. It would be a glorious day if my stomach held.

It was, I walked and ate for close to 8 hours wandering about, looking at kitsch and sampling gastronomic delicacies. I was also thinking about my sister Amy. It was a week past the 3 year anniversary of her death; she was 36 when she died. She died of leukemia and unfortunately for her my slacker stem cells just didn’t do the job. I had been trying to come up with a gesture, a token nod to the universe and her about her life and outrageous spirit when I passed a cigar bar. Now that is interesting I thought, looking back over my shoulder heading toward the eyebrow threading salon.

Ten years ago on a trip to Austin to visit Amy, we went to one of her local watering holes and I met her friend Lorelei a good ol’ Texas girl. We settled in on the back deck of the bar with our Shiner Bocks in the cool of the evening. As we relaxed Lorelei and Amy pulled out cigars. Amy was not a smoker; she didn’t ever smoke cigarettes to my knowledge. To see her prep a big fat cigar made me speechless. She and Lorelei grinned at each other and lit the tip. I cocked my head at Amy and she gave the only answer she could. “It’s the only 8 inches that never done me wrong”. With that we laughed and drank the night away, the tips of the cigars glowing red into the night.

Flash forward on my downtown eating adventure I had passed both a cigar shop/bar and a cigar café in my travels that day when it hits me. I have to man up and smoke one for Amy. I will need an extra-large adult beverage for this to be possible but I can pull my skirt out of my back pocket and butch up. I find my way back to the cigar shop/bar. It has been years since I was in a smoky bar; I hadn’t missed it at all. I approached the guy at the counter and tell him I wanted to buy a cigar and he led me to the vault, or the humidor hookey dokey. It was smoke free, ahhh. He asked me what I would like.

“I don’t smoke” I stammered “but I want to smoke a cigar in memory of my sister who died, she did smoke them”.

I choked up at the end, an unexpected and unwelcome emotion at that point in time. I am clueless about my inner workings most days and would like to keep it that way at least in public.

The counter man found me a honey flavored cigar which is great for folks who don’t smoke. Evidently there is a market for non-cigar smokers who smoke cigars. Who would have thunk it? I paid for my stogie, he clipped the end and I took a pack of matches for the road after declining his offer to help me get lit. I needed a drink for that, thinking how hard can it be anyway I have seen it done in tons of old movies. Besides it was too smoky to stay in the bar and smoke it. I know that sounds crazy but if the shoe fits. I was determined to find my way back to the second place I saw which was an outdoor/indoor cigar smokery and libation establishment.

After a little while of wandering I found it and settled in after placing my order for a martini with three olives. Hey, three gin soaked olives are almost a serving of vegetables, and hell I might have two martinis’ which definitely takes it up to a near healthy meal! I had an ash tray at the ready and started the process of lighting a cigar on a windy afternoon. My cursing like a sailor at my first three attempts completed a lovely picture. What can I say I went to the Ernest Borgnine School of Charm. Once lit or half assed lit as only one side was burning, the other, well not so much I called my trusty side kick Marsue in Denver for company on this journey. I sucked hard as the phone rang in Denver; finally I had gotten the whole damn end to light up. As Marsue picked up the phone the waiter delivered my martini and I thank him.

“Guess what I am doing?” I said looking down at my newly delivered drink.

Marsue gave some smart assed answer but it was lost on me as the waiter had delivered a Green Apple Martini with three olives. Yikes! I flagged him down and explained this cocktail was not only not what I ordered, it was also an abomination against all that is good and shaken not stirred. Marsue hears this interchange laughing and then I tell her where and what I am doing. She cracks a beer to help me celebrate Amy’s life, well lived however short.

I was trying to puff and talk but there were problems. One big one was me.

“Damn it’s gone out” I mumbled around the wet end stuck in my mouth.

“You have to keep working them so they stay lit” Marsue said. Is it any wonder why she is a perfect partner in crime?

Evidently cigars require more attention and up keep then my roommate Hector the Beta fish. I got the damned thing lit again after three more matches and was then vigilante about keeping it going as we talked. I noticed the double takes now from mostly men and as I was at the finish of my second Bombay martini made to icy perfection. I sighed and signaled for the check, I was also at the end of the honey cigar. The sun was starting to dip behind the building and it was time for me to walk off my cocktails and think. I said good-bye to Marsue and thanked her for the camaraderie. She is the kind of friend that comes along once in a lifetime if you are lucky. She is smart and sensitive always knows what to say and what times not to say it. I wish I had that skill, but I don’t.

I smelled like a bus station in the 1950’s minus the urine, I stank from smoke. I didn’t regret smoking the cigar at all, it was great fun. It was a little gaggy at first but hey I am sure Amy got a huge laugh over it. The things I do regret are the things I don’t do, things I am scared to try, never what I do. It turns out that is not uncommon, though most people might not realize it. People agonize over what they do and do badly. But in the end it seems according to the author and Harvard psychologist Daniel Gilbert in “Stumbling on Happiness” what we regret most are things we did not do. There are no guarantees in life; it is a short, slippery, and full on roller coaster ride. Not too long ago I was talking to a young girl who was cutting my hair. She wanted to know how I moved from state to state and had so many different careers. She thought I was brave, adventuresome, and smart. I could be, I could also have ADHD, but mostly I told her I am comfortable making mistakes. I make them all the damn time. I would rather try something, dive in and make a fool of myself, get hurt by love, naivety or bad fashion choices than sit the ride out. Amy taught me lots of things, laughing is always a priority, the purple ice cream at Friendly’s is a damn tasty treat, looking ridiculous at any given moment is easy to achieve and easier to survive. Not living every day with whimsy, passion and an occasional good cigar is a crying shame.