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20 First Dates - Part Six, Valentine's Edition

Today should be a fun (for me) post – the time when I am finally going to speak about MY 20 FIRST DATES, and what I learned, before delving into the amazing journeys of contributors and their dates.

It’s a fun post, but also one I have hesitated to post because on my journey, I found LOVE; and honestly have been so wrapped up in a new normal, that while it’s been weighing on my mind that I shut readers out after taking them partway, I just haven’t taken the time to continue writing about the journey from there to here.

However, today is the second anniversary of the first date I went on post-filing. I don't know what either of us was thinking, going out on Valentine's Day, but it seemed apropos to start writing again about the dates, on this anniversary, after a hiatus.

There is so much more to share, and I wonder how much to share about the actual dates, since that isn’t what this is really about, and how much to share about the lessons I’ve learned, which is what it is really about.

I wonder if any of the dates that I am still friends with will read these words, see themselves, and offer a rebuttal.

Seeing myself spiraling down the rabbit hole, I now take you back to the dates themselves before I digress further, or convince myself to stop writing.

So, here goes... I have friends who have thought this process is asinine, and others who have thought it’s brilliant.

My belief is that without this process, I wouldn’t have challenged myself to step outside of my comfort zone, take a chance, and figure out exactly what would make my family and me complete.

One of the most fun parts of this journey wasn’t the actual dates, it was the debriefs with my girlfriends. We have had many, many laughs about the journey, the stories, the photos sent inappropriately...

A huge shout out to my wing women, some of whom are below, celebrating our baby wing woman's marriage!

For these debriefs the only way to keep track was to nickname the various participants. The nicknames varied from hobby, to profession, to geographic location. (Some names have been changed to protect friendships I still have with a few of these fellows.) Nicknames such as P, SP (the literally shorter stature version of the person with the same name), Hair, Oiler, Real Estate, Grandpa, Special Forces (Australian), Aspen, Frenchie, Techno, MacLaren, Uber, Spaniard, Dad Bod, and Tattoo; the list continues.

I decided to say “yes” to dates with people I may not have originally considered. I accepted dates from Bumble, dates from Facebook “friends”, and dates from personal set ups. I sometimes gave people multiple chances/ dates before ruling them out. I also learned to say “no thanks” or chalk things up to bad timing, if I did not want to go out with someone again. I went out with a span of people ranging in age from mid-20s to mid-50s.

There’s a touchy subject, which must be touched upon. As a recently single woman who had been in a monogamous relationship for almost 18 years, it was really important to me to:

  1. Get tested for everything under the sun, regardless of monogamy;

  2. Make sure I was protected (thank you Planned Parenthood for the IUD) from unwanted pregnancy; and

  3. No matter how many different people I was dating, to be sexually monogamous. This is absolutely no judgment on anyone else and their decisions – it was just important to me, although I highly recommend at least the first two.

A random sampling of dates that didn’t end up

going well, or anywhere…

with a little bit of “where are they now"

After lots of texting, go on a brunch date with “Leno”; he was hung over (never a good start), we brunch at a spot that was a lot more expensive than I realized (under new ownership, now closed), conversation was stilted, yet he still thought dating would be a great idea. Shortly thereafter I decided to date someone exclusively, which makes him upset that it wasn’t him. (“Leno” recently reached out, about a year and a half after one and only date, to see if I was still in a relationship or “had seen the light” – didn’t have the heart to tell him that I wasn’t in the same relationship but did tell him I was engaged. Response was jokey/ defensive. Refrained from responding.)

Texting with man from Bumble, who also has children. Tell him about volunteering with my daughter at AniMeals. Man and daughter show up, as does ex-boyfriend. Awkward situation becomes worse when ex-boyfriend has parked by your car, and mini-me doesn’t like him (because he wasn't a father and always wanted to go clubbing, when all she wanted was attention/family time), and he walks you back to your car, asks you out, and man from Bumble later asks who the guy was. Go out to dinner with man from Bumble, he thinks you’re the cat’s meow, and you definitely don’t think he is, so tell him the timing is bad.

Set up breakfast fundraiser for day job; man helps me carry donations to car, gives me his card, calls me ma’am, and asks me out. Time passes, man finally decides to call and admits it was my ass in the very work appropriate dress that made him ask me out. Go on date, find out his ex is an alcoholic, watch as he proceeds to get wasted, and wonders why I don’t want to go out again. It’s too bad, because I really think we could’ve been friends.

Lunching with Boxer, whom I had worked with on a project during Super Bowl. Mutual attraction. Boxer is from a prominent family, lives in the suburbs. After date, he texts that if we got married, we’d have three kids and four dogs. Boxer asks friends about you at events, and watches your Facebook/ Instagram, but Boxer is also in his late 20s, and you honestly don’t see how it would ever work. Especially when dates, to you, should start with being properly asked out, and not just randomly texted and asked about. (Boxer recently texted in surprise that I am engaged, and hoped my fiancé realized what a prize I was…)

Probably the favorite of the friends who met him, Spaniard was a Bumble date who patiently waited at least a month or so to actually get a date nailed down with me. He took me on an amazing dinner, told the restaurant it was a special occasion, and treated me well. Spaniard was a workaholic who lived in London but was/ perhaps still is on a very long project in Houston. I never called him my boyfriend, but realize in hindsight he may have thought he was… enjoyed our time together and did consider dating only him; but looking at my life and knowing he would eventually go back to London, decided to call it quits. Spaniard was very bitter, but started dating someone else quite shortly after, and recently reached out to tell me he was in love, and wanted to marry the woman and they had agreed not to keep in touch with exes. Then proceeded to admit that it was his decision not to keep in touch with me. I wished him very well.

There were many others with whom I started conversations and I didn’t ever meet, because that is how life works and it is not always easy to fit dates in, when you’re a single mom with a full life. Ultimately, I am exactly that, a single mom with a full life. There are many, many men for whom that won’t work. For the right person, it becomes much more simple and it just does.

One that I’m still friends with (we’ll call him Harvard) and I had many conversations about how our chemistry was amazing, and our love of talking “shop;” but in the brief time we dated, I learned that I would always come second to business, and that he didn’t like dogs, and that whether he admitted it or not, he hid his feelings behind his incessant need to achieve. Many women would put up with this because, perks. There can be many amazing perks to dating or being married to a man like this. For me, there has to be some give and take – I recognize that I tend to be very focused and driven about work as well, but the dogs, those are non-negotiable for my daughter and me. In the end, both parties have to be willing to compromise and communicate about wants, needs, desires, and figure out the inner workings of the relationship together, for it to truly work. Harvard did reach out to congratulate me on the engagement.

Before meeting the person of my dreams, I met someone at a charity event whom my friends had been telling me would be the perfect person for me (we’ll call him Art Lover). We ended up finally finding time between our schedules to meet, and yes, it did seem we would be “perfect”. We shared a mutual interest in art, a mutual interest in celebrating those who make a difference, and a mutual attraction. We both could see what life could be like with each other. I met his children. We introduced our business partners to each other to see if we had production synergies. I gave him a tiny but treasured piece of art from a favorite Los Angeles artist, Stephanie Mercado, for his birthday. He was shocked that I “got” him. And I’m sure, scared. He asked me to wait and assured me that “this is happening.” I did, for a bit, until I realized that wow, this really isn’t what I want. If someone wants to be with me, they’ll make time to acknowledge me and make time for me, even if their schedule is just as much as mine.

Interestingly enough, I have recently heard from several of the 20 First Dates. Not just Spaniard or Boxer or Leno, but also MacLaren, Tattoo, and Military. It’s strange how you can stay in someone’s texts and pop into their head again.

I wonder what inspires them to check in and see if someone (me/anyone) is still single (or still in a relationship) and if I’d like to go out again, in some cases a year or more from the last time I saw the person.

Nostalgia is an easy place to live – I’ve been there myself.

I no longer find myself there, and in a future post I’ll tell you all about it…

Stay tuned!

Written by Anika Jackson. Mother, community volunteer, philanthropist, and socially conscious fashionista ambassador. VP, Strategic Partnerships, Real Beauty Real Women, and CEO of Philanthropic Fetes. Check out, Social Graces Social Club

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