I have come to the point in my journey where friends and family are encouraging me to date. Even I, can finally get my head around the fact that I am ready to start meeting a potential partner. But the thought of jumping into the dating pool is enough to make me curl into a ball and suck my thumb. Fifty years ago, people met in bars or were fixed up by friends. Today, you have to go online, make a profile without lying too much about your age, put up some pictures that make you look hot (or at least acceptable), and then wait to be “winked” at or “faved,” or worse, swiped off the face of the app!

Many widows and widowers feel that dating is a betrayal of their loved ones. Some feel that it is exhausting to start over and make small talk when conversation flowed so easily in a marriage. Many don’t feel they can ever replace their loved one. Grief is unique to everyone. There is no magic answer to the question “How do you know when it is time to date?” Finding the right time to start dating after a loss should be up to you, and you alone. Shoulds must be tossed out the window. Try not to listen to others who say it is time you started dating. They are not in your shoes. This is a complex and difficult step in your journey of grief. You must be the arbiter of this decision. You must weigh the pros and cons and examine all the reasons you are finally ready, or decide whether it might be too soon to venture into the dating world, where you are out there and subject to rejection and possibly further pain. You have to be strong enough in your own self-worth before you can fly away from the nest of grief into the newfangled dating arena of today. You clearly must fortify yourself against the negative pitfalls of being rebuffed.

It is over two years since Peter died, and I am at last venturing into the dating world. I am ready to do this because I know that Peter would be the first one to tell me to be happy. After two years of grieving, I know he would want me to venture out and try to meet someone who would make me laugh again or at least buy me a nice dinner! I am aware that dating is not the cure for loneliness, but I might find someone to add joy to my life. I was definitely ready to try. I made sure to be up front with my family, and they were on board with me getting out there.

Since the dating pool at my age is pathetic, I decided to join a dating site to widen my horizons. If I am to find companionship, then I have to venture out and experience online dating. Besides, the laughs alone had to be worth it. My girlfriend and I checked out the possible candidates on JDate, and we fell off our chairs in guffaws, so I decided to try a site geared to the over fifty set. Setting up my profile was quite the task. I had to fill in lots of questions. The first question was “Looking For,” and the choices were marriage, serious relationship, travel partner, casual (I assume this is dating-site code for “hookup”), friends (with or without benefits), or pen pal. Why would I plunk down money for a dating website for a pen pal? I had one of those in grade school, and she lived in Denmark! I filled all the requisite boxes, put up a few pics, and paid for a few months. Within seconds a barrage of pictures of elderly gentlemen way over fifty appeared on my “views list.” I realized they were retirees, but didn’t they have anything better to do than troll this website at 7:30 a.m.? I was hit on by eighty-five-year-olds and forty-five-year-olds. Who knew I was a cougar? Lucky me! I eliminated all the right wingers; the ones who hadn’t finished high school; those who were never married; the “social smokers”; those who loved their cats, snakes, and ferrets; the one who put up his profile picture wearing short shorts while seated in La-Z-Boy lounger; and the one who listed his occupation as a “stay at home clown.” You can’t make this crap up!

After this horrific experience, I heard about a matchmaking service called “It’s Just Lunch.” I wanted a way to meet someone without sifting through the rubble of the Dumpster-diving dating pool. I didn’t want a hookup site like Tinder that would require me to swipe prospective dates—or worse, get swiped! The interview was quite lengthy, which was a good sign. They asked me what qualities I needed in a future date, and without hesitation I said, “Politically liberal, a sense of humor, and someone that was pleasant looking and preferably taller than I.” I waited for my dating consultant to call.

My first date was a disaster. It lasted under an hour. Al (names changed to protect the innocent—although not innocent in this case) greeted me by saying, “You are attractive. Why would you use a dating site?” Really? That’s your opening line?

He volunteered nothing, so I asked him about his interests according to the description sent by my dating consultant. “I hear you like cooking?”

He replied, “No way.”

“I hear you are seventy,” I said.

He answered, “I lied.”

I said, “I hear you are recently divorced?”

He said, “I’ve been single for over thirty years,” code for “I am looking for a hookup.”

Al never looked me in the eye, never asked me anything about myself, and didn’t know I was a widow, which I blame on the dating site. When the separate checks came, he didn’t even look at the tab; he just said, “Separate checks, a great idea!” I understand the concept of separate checks on a first meeting, but c’mon! At least offer. This guy’s largesse level in moolah and spirit was at ground zero. When I almost ran out of the restaurant after he said he didn’t want coffee, he exclaimed, “Tell them you liked me so I can see you again.”

Without hesitation, I scowled at him and said, “You must be joking! Not unless hell freezes over!” That is the whitewashed version of what I actually uttered! If he were an Uber or Lyft driver, I would rate him with no stars.

Date two was slightly better, but that is because the bar was so low. As I was driving to park for my date, which was dinner this time, I saw an older gentleman listing like the Leaning Tower of Pisa as he walked, trying to get to the restaurant. Yup, this was Alex, my next candidate. The old dude was four years younger than I, was sweet, and insisted that he would pick up the check. Turns out Alex had only been married once, for about a year. The evening tanked from there. There was no spark, chemistry, or even a pulse. Alex liked handicapping horses, reading, and watching television in bed while chewing Nicorette gum. I decided quickly that lunch was an easier out! Unless it is It’s Just Drinks, I am not on board with It’s Just Dinner!

Date three was an Australian dude who loved to pilot his canal boat in Europe. He proceeded to tell me about his multimillion-dollar ranch in Northern California, the nineteen buildings he owned in Los Angeles, and his house in Venice, California. I couldn’t find a single thing we had in common except for food, which he relished as noted in his ordering of two glasses of wine, grilled salmon, and two desserts. I ordered a salad. The check came, and yup, you guessed it, he announced we were splitting it. With all his talk of money and property, he didn’t even have the kindness to offer to pick up the check!

My final date followed the disaster pattern of It’s Just Lunch. Sean arrived wearing a stained and tattered jacket over a never washed Hawaiian shirt. He was a psychologist so I thought he might be more empathetic. He never complemented me on my looks, he never made eye contact, and he never once asked me about myself. I was out of there in one interminable hour. So far, It’s Just Lunch is out to lunch! I decided that dating sites suck at my age and that if I meet someone, it will be through a friend. Dating sites are great for younger people. At my age, they are looking for a nurse or a purse!

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