How I Re-entered The Dating World… Hello, Old Boyfriend!

Guest Blogger: Sixty And The City
Post divorce, my first date was with my boyfriend from senior year in college which was of course,  five years before that date. Yeah, right!, How about almost 30 years? Do you think that I looked the same? The good thing is that we had kept in touch intermittently so we both knew that we had not stayed the same.
I had been separated and divorced for over a year but had not been on one date. Wasn’t ready for the whole doo doo dance and quite frankly, was still licking my wounds from my scorched earth marriage and divorce. Also, I was absolutely not telling my adolescent kids that I was even dating.
It was tricky; but they had no need to know and I had no desire to make them part of the process. Many women disagree and parade a countless array of guys in front of their kids. Can you imagine, “mommy has new boyfriend and another new boyfriend and another…how’s about NO?<
Do yourself a HUGE favor: DON’T do it.  At least until you’re actually a couple. THREE dates does not make a couple. More on third dates at another time. My daughters did not meet anyone I dated until they were in college. Ok, I am overprotective. Sue me.
Anyway, back to my first date. For some reason, I was sitting at my desk one day, working, not really and thought of this guy. I had his office phone and with shaking hands, NOT KIDDING, I picked up the phone and called.
Almost hung up when I heard his voice but thankfully, that little voice in my head, in my case the very loud, shrill inner voice said, “Dummy, take a shot”; and so I mumbled hello and off we went conversing as if no time had passed. Coincidentally, and legitimately, I really didn’t know, his marriage had crashed and burned, too, although, he hadn’t gone through the whole process yet. Now, hold that thought, I will get to it.
No sooner did he say that he was “free”, we were planning dinner at the Union Square Cafe. Great, I said to myself what in hell was I going to wear? After discarding nearly every article of clothing I owned, I finally settled on understated and FABULOUS. Was there any other choice? Since I am all about making an entrance, I came in after he had been seated. I made one hell of an entrance.
He still looked good really good. Never classically handsome; but way cute and sexy with a delicious twinkle in his eye, and a smile that could make one’s heart melt. You get the picture. Picture Robert De Niro circa Godfather Two plus 15 years without the guns. Be still my heart.
Sitting over dinner, we chatted about the usual things: kids, life, work. No discussion of my ex and his “almost” ex.
Rule One:
First, or even fifth dates, are not the time to list every grievance you had with your ex. Why bring up a bad meal? Plus, it really is not interesting conversation and one risks sounding like a miserable harpy. If you are a misery to be around, work on it before you venture on your first date.
Being with Steve was comfortable and scintillating. We were able to jump over the “getting to know you” part of the menu. We had already been on hundreds of dates. Ok, it was 30 years ago but let’s not nit pick.
It was intoxicating and  so damn fun. He was funny and he thought that I was the funniest person he had ever met. Smart guy. Additionally, he thought I was POSITIVELY NO HOLDS BARRED, FABULOUS. Did I hear gorgeous, anyone?? Earlier, on way  to our first date, I was trying to figure out how to iron my face before I got to the restaurant. I prayed for ambient lighting. Luckily, he didn’t see the current me but rather the young girl whom he had fallen in love with in college. Ditto for me. He was crazy about me a gazillion years ago and apparently, it hadn’t worn off. Could I pass out now just writing this??
Rule Two:
If you get to choose where you are meeting for that oh so special first date and even if it’s an old BF, who knows you,  do yourself a huge favor and please pick a place where you will look positively incandescent as opposed to green under hideous bright lights where every wrinkle and flaw is visible.
We sat and talked for hours and when he kissed me goodbye, I almost plotzed. He was a world class awesome kisser plus, I hadn’t been kissed in years and certainly not like this. I had to get going to begin the epic poem of getting home to NJ. For once, I didn’t whine about being in the bus as I just sat there in la la land going over the date for an hour as I knew when I got home, it was back to mommy-land and trying to remember what story I had told my two delicious dollies about where I was that night.
Before I got home, he called me to tell me what a great time it was and when were we going to see one another again. Had to figure out my next lie to my kids so didn’t set-up the next date until the following morning.
Right now, I cannot remember where we went the second time; other than it was a very romantic place in Soho. Quite frankly, it could have been McDonald’s with great wine and soft lighting. Who cared about food?
That part of the evening went by in a blur. Yes, I was acting like a besotted 20 year old and damn did if feel great. Without missing a beat and in a way that didn’t make me have a complete panic attack, he suggested that we go back to his apartment, which was actually the apartment he grew up in and had inherited from his parents. I declined as it just felt too weird. If felt too much like déjà vu all over again. Kudos to yogi for that expression.
Next thing we are at the Gansevoort which btw, is blissfully dark. Ok, the Gansevoort: we brought up the median age by at least 20 years but who cared? As we got into the elevator I started to feel like i was going to pass out. Was I really going to get undressed in front of someone who knew me when I was 22?? Now mind you, I was a chubster in college but young is young. I had held up well and was much thinner but geez, I had had two babies and eaten my way through many decades. Whose body was this? It’s still something I ask myself on a daily basis.
While I was hyperventilating in the bathroom, he had ordered up a bottle of excellent champagne. I sorted through outfit choices in the bathroom. I tried on the shower curtain but there wasn’t enough coverage. Where was my burka when I needed it? Oyyy, now what was I going to do? I came out of the bathroom tripping over the three towels and the bathrobe that I so elegantly wrapped around myself. Charming.
After my initial hysteria and two glasses of dom, i got over myself. Kids, it was like time had stood still. Always fabulous, he had gotten better with age. Is that even possible? I NEVER wanted to go home but kids, job etc beckoned me.
Side Bar: Thomas Wolfe said: “You can’t go home again.”, and there is some truth to that but home it was, except not in his mother’s apartment and it was delightful.
What followed can only be described as a true love affair We were crazy about each other all over again except this time, it was even better. We acted like kids and it was pure unadulterated bliss.
Not long after we started seeing one another, my kids went away to camp. Now, I love my kids more than anything but FREEDOM and no sneaking around and lying. He came and stayed at my house and I cooked glorious meals for him. Nothing beat it.
Of course, reality came mid-August when the kids came home but I had missed them and was thrilled to have them home and hell, what was bad about going to every gorgeous hotel in NYC? Yup, I still hadn’t gotten over the old apartment thing. Mind you, it was lovely with a gorgeous East river view but for whatever mishegas (cup of crazy for those not familiar with Yiddish), that old apartment had too many ghosts.
This man wrote me love letters; or should I say love emails? OMG, just thinking about them now, I get weak at the knees. It’s hard for many to just say those three little words; “I love you”. Well, blissfully, not this guy. I had hit the motherlode and I was beyond happy.
For over a year, we both walked around with a perpetual smile on our faces. With his kids, and my kids, and jobs; we didn’t get to see each other as often as we would have liked but that made every time together more precious.
Well, my friends, be still my heart, around the bend was a big fat problem about which I was totally unaware. In retrospect, there were some hints but I chose to ignore them. Of course, I did. Reality was not going to spoil my buzz.
By this time, of course, we knew all about each other’s kids and much of the details about our unsatisfactory marriages and my shit storm of a divorce. He never mentioned any details about his separation, which I should have taken as a warning sign but NAH, as above, reality is highly overrated.
One of the things that I most adored about him amongst many was his unabashed love for his daughters. His mother’s apartment was a few blocks away from his girls and he saw them several times a week. A man who is devoted to his kids is a man we all want to love.
We were sitting at lunch one day and next thing I know, he is crying about his kids and how much he missed being a part of their everyday lives. Unlike my usual loquacious self, I listened until he was done. All the while willing him silently to STOP. The last thing he said nearly blew me out of my seat. All I can say is it was good that we were in a public place as it held me together. He announced that he was moving back home because of the kids. Did he love me as I loved him? Without question but he needed to be with his kids. I tried to talk to him about it but clearly, this was not a decision that could be changed by the cajoling queen.
We hurriedly settled the check and came out into the blaring sunlight of Broadway/38th Street. For once, I wasn’t obsessed with lighting. I had to not freak out because in those days, I was bound to run into several people I knew from my industry on the street so sobbing hysterically and holding onto his leg (figuratively) while trying not to vomit was not a plan.
He hugged and kissed me goodbye and literally I felt like I was going to drop dead on the spot. We actually did see one another a few times after this because neither one of us was prepared to say goodbye. The last time this man kissed me goodbye is something I will never forget.
Clearly, I was devastated. The good thing is that I had two kids for whom I was totally responsible so going to pieces was not an option. Plus they had no clue about Steve and I; and I was in no mood to do a post mortem of this relationship with them. Actually, almost no one knew about it. Yup, old blabbermouth can be very secretive and private.
Thankfully, I am resilient so I pushed myself through what I was feeling. Spent a lot of time in the bathroom with the shower on; sobbing into a towel, but I got threw it.
Was I happy that I had taken the leap with this man as my first foray into the world of being a middle aged single woman? NOT EVEN A QUESTION. As a matter of fact, I would do it again, even knowing the outcome was not going to be what I wanted. I was lucky to have found him when I did. Also, it reminded me that I not only could love someone but could be loved back.
Moral of The Story:
if you have some old boyfriend, look him up, as you never know. Keep your eyes and heart open.
Next Stop:
On-line dating. Of course, it took me over a year to jump in. Talking about reality testing. UGH!
BTW, very recently, my oh so clever eldest daughter, turned to me at dinner and said, who was Steve or some such thing. So much for lying to one’s kid. How in the hell did she know?  It was the stone age. We talked on a LANDLINE and she listened on the extension. Gotta love her.

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About the Author:
Ellen lives and works in NYC. Her blog Sixty And The City takes us on a poignant and funny ride of the dating scene after 60. Follow Sixty And The City on Instagram and stay tuned here on Kuel Life for more anecdotes. This blog has been reposted with permission from  Sixty And The City.