My Last Valentine’s Day Being Single at 40 Years Old

The last Valentine’s Day I spent as a single woman, I was 40 years old, and it was with my now husband, Darryl, in February of 2017. Despite having known him for 14 years, it was the first time that we had gone out together on Valentine’s Day. Up until that time, we casually and intermittently dated, and while we previously shared kisses and feelies, we had never actually had relations. We reconnected about eight months prior to this Valentine’s, in the summer of 2016, by happenstance when I almost hit him driving in a shopping plaza parking lot as he was walking back from picking food up for him and his parents.

At this point in my life, I was a successful attorney, but I was also still processing the effects of a wounded heart from a previous long-term, situationship. To be honest, I wasn’t even expecting to have a Valentine’s Day date or gift that year. Normally, in the past, I would have been sad that I was going to be alone on Valentine’s Day. But that particular year, instead I felt very empowered, confident, and settled in the fact that I was single, re-discovering myself, and celebrating finally being strong enough to cut ties with my long-term, ex-boyfriend.

Later on I learned that my husband always took a woman out on Valentine’s Day, but for whatever reason, I had never made the cut prior to this year. And that was okay considering that I was pretty much in an on again off again relationship for the previous 10 years. However, when Darryl asked me out for Valentine’s Day this year, I was taken aback because up until a few days before he asked me, we hadn’t even talked about going out on Valentine’s Day. I assumed that he already had other plans as we were both engaging with other people at the time.

After agreeing to being each other’s dates for the Love Holiday though, I will never forget being in court the day before our Valentine’s Day dinner and seeking the opinion of the judge and the opposing counsel before our hearing as to gift suggestions for Darryl. I specifically remember the judge stating that I should get him some socks because they were practical, and men could always use them. I pondered the judge’s answer and thought that was very rational, but at the same time, getting socks just did not feel right. Ultimately, I decided to play it safe and bought Darryl a medium sized box of chocolates.

Our Valentine’s date that year wasn’t anything spectacular. It was an early dinner because I was a single mother of a 14-year-old daughter, and I had to get back home at a decent hour since my father was watching her while I was out that evening. Darryl and I met at a Mexican restaurant and when we arrived there was no one else in the dining area, which was fine with me since I am not a big fan of crowds anyway. We immediately exchanged the obligatory customary boxes of chocolates to one another, apparently both of us choosing to play it safe.

Per our normal interactions when we either spoke on the phone or got together, Darryl and I spent several hours at the restaurant, talking, laughing, joking, and playing, totally oblivious to the fact that the dining area filled up with people now waiting for a table. I left the restaurant that Valentine’s Day thinking that Darryl had become a renewed relationship prospect in my life so the next day I invited him to watch the NBA All-star Competitions at my house that coming Saturday. He acquiesced and I made dinner and the perfect sweet tea, which was what he always ordered when we went out to eat.

If you talk to Darryl now, he will tell you that night of the All-star Competitions was the night he unknowingly started to fall in love with me. After the competitions, we stayed up to the wee hours of the next morning talking about sports, music, TV shows and how privatized prisons perpetuated a criminal system that targeted and imprisoned minorities for the same minor drug offenses that our non-minority counterparts would be released with a warning if they were caught high, drunk or with drugs on them if they were stopped by law enforcement officers.

Anyway, after having a great night of fun and stimulating conversation that weekend, I later asked Darryl if he had any plans for his upcoming birthday, which was in the beginning of March. He stated that he did not, and I offered to take him out and celebrate with him. I planned an amazing birthday for him. At least in my mind it was amazing. We had dinner at a Caribbean styled restaurant that had a live band playing and singing hits all night, I reserved a hotel suite and had a delectable cake that ordered earlier that day, delivered to our room, which was there when we arrived.

Knowing one another for 14 years and going out countless numbers of times and speaking for I don’t know how many hours on the phone over the years, I planned for “it’ to go down that night. After presenting Darryl his birthday cake and singing happy birthday, the Marilyn Monroe version of course, I left the room, and returned after changing into some lingerie and heels. Undoubtedly, we consummated our relationship for the first time that evening after knowing each other for such a long time. In between one of our sessions that night, we began talking and I asked Darryl about dating one another exclusively.

I thought I had just put it down and he would immediately respond excitedly with a resounding “Yes,” but he didn’t. But he did not say “No” either. Instead, he calmly replied that he would think about it. WTF?!?!? And he did just that. He thought about it for almost 3 weeks. He thought about it for so long that after a couple of weeks without an answer, I made up my mind to basically dismiss Darryl and cut ties from him. I refused to bring the conversation back up again as to whether he thought about my proposition. We both knew that I had mentioned dating exclusively a couple weeks earlier. I thought he was just avoiding the subject, but the exact opposite was happening.

Just when I finally decided to end this once and for all and continued to communicate with other men, Darryl and I went out to what I planned on being our last date. After eating lunch, Darryl casually remarked that he would like for us to be in an exclusive relationship. My mind had already processed him out by that time, so excitement was not my first response because I needed to process that information again and get my mind to where it was a few weeks before he finally gave me his answer. It took me a few days, but I finally began to relish in the idea and thought of Darryl and I exploring something more serious between us.

The most obvious point of this story is that sex does not equal a relationship, regardless of how wonderful your bedroom skills. We all know that, but it never hurts to reiterate that fact. Second, we as women, especially as successful and career-oriented women who are used to getting our way in many other different areas in our lives, need to practice patience when it comes to matters of the heart and becoming involved in healthy relationships.

I did not press or nag Darryl on the commitment issue. I wasn’t even going to officially tell him that I would no longer speak to him. I was just going to disappear and fade into the background and let him figure it out. Darryl and I both knew I asked the question a few weeks before about becoming exclusive. We as women need to realize that just because we have envisioned a man being ours or being in a relationship with him, he may not have processed all of that at the same moment that you did.

It is important to control your desire to push, remind and persuade a man about being in a relationship or even getting married to you. And giving a man a relationship ultimatum is a huge “no, no.” When or if a man is ready to be in a mutually exclusive relationship or marriage with you, he will let you know. Constantly or even periodically bringing it up every so often only delays his response to your advances if he is in fact considering a relationship or marriage with you. Men do not like to feel rushed or pressured into anything, especially into a romantic courtship or marriage.

As for Darryl and me, less than a year after that Valentine’s Day in 2017, we were married and expecting our first child together and then subsequently had another child after that. I was 41 when Darryl and I both got married for the first time and when we had our first son together. I was 43 when we had our second son together. Both boys were born healthy, and I don’t regret getting married to Darryl after I turned 40 (we initially met when I was 26 years old before I even finished law school) or the way that our lives turned out together as a couple. He’s a great guy who thinks, and oftentimes over thinks, all major decisions in his life. Him committing to me was a major decision that paid off for both of us.

Now, notwithstanding all of that, I will say, that despite taking that first step towards committing to Darryl, there almost wasn’t a marriage or children with him. While I was no longer in a relationship with my ex-boyfriend when Darryl and I started dating exclusively, I also was not completely healed and over him either — yet I totally thought I was. I almost destroyed my future with Darryl because I didn’t do what ALL women need to do before they become involved in a new relationship, especially in their 40’s.

That process and discussion is for another conversation, however, the purpose of me sharing this experience is that patience is absolutely and unequivocally a virtue. Being direct, chasing, and never taking “no” for answer when it comes to pursuing a professional goal or milestone is without a doubt a necessity. But that same tenacity turns off many men when a woman is trying to show her interest in taking a relationship to another level with a male prospect.

Always keep your dating options open until a man is ready to be in a mutually exclusive relationship with you. With the path that my love life has taken, I can truly say that 40 was just the beginning of my Happily Ever After 40 journey and the best is yet to come.

For more dating and relationship tips and coaching by Tamika Michelle for successful, professional, and educated single women near or over 40 years old who are Bosses by day but single at night, visit www.TamikaMichelleJohnson.com, where I work with women to break bad dating and relationship habits and teach them how to attract quality men in order to have quality relationships.

T. Michelle Johnson is an Attorney, Podcast Host, and Empowerment Speaker for Women Over 40 Years Old