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Sex And Relationships

5 Lessons I Learned From Dating After A Divorce

Published:

October 4, 2020

I finally got the courage to start dating about 6 months after I separated from my husband.

We hadn’t filed for divorce yet … but I knew I needed to get out in the dating world. Or, honestly, it was more like my friends told me I had to. If it was up to me, I would have hibernated in my apartment for the next year. I was terrified on so many levels. I hadn’t been on a date since 2005.

In 2005, I was in my mid 20s. That’s when you went to bars (without masks!) and met people the old school way. And you were carefree and casual. Dating apps didn’t exist. I was running rampant “Sex and The City” style from bar to bar.

Oh my. Things have changed.

I remember my foray into the digital dating world really vividly. I was coming out of a very depressed 3 months after learning my husband was having an affair. I had convinced myself the best plan forward was to move to a small village in Mexico with my dogs and give up on men and eat tacos all day. I was pretty committed to this idea and I thought it was pretty rationale. I don’t think I had left my apartment in months.

My friend Stephanie (who is about ten years younger than me), sat me down and literally forced me to create a dating app profile. She convinced me that I didn’t have to actually go out on a date, but it would be helpful if I could just swipe photos all day. And then eventually I would realize there are actually other people in the universe I could theoretically date. And maybe then I wouldn’t have to move to Mexico.

It was horrifying. But she was right. And I am grateful to her for forcing my hand into the internet dating pool.

LESSON 1: Create dating app profiles. Even if you are not going to go out on a date. It will give you your confidence back.

I was quickly schooled on the “photos” I needed for my profile. The “bathing suit” shot,” the “group” shot. The “prove you are fun” shot. I had no idea so much science went into the underlying communication that needs to be done through each photo.

I was quickly told but my friend Carole, whom I consider a dating expert, that I was doing a bad job. She schooled me on the app dating rule #1 – that every girl needs a “bikini” shot. Thus, the impromptu beach photo shoot after she told me my Hinge and my Bumble dating profile “sucked.” She quickly critiqued everything that was wrong. I listened intently. I needed to know the new dating rules if I was going to survive this new world. She orchestrated a Bumble photoshoot.  My bikini pic was live.

I had recently turned 40. I learned my husband was having an affair with someone less than half my age, and in all honesty, my confidence was shattered. And now I had to post “bikini shots” on a dating app.  I felt ridiculous.

Side note: someone should start a consulting service on your dating app profile. Apparently it’s an art form to carefully select each image and its underlying “photo messaging.” Carole – I think this is calling your name.

After mastering my profile, I had to learn the new landscape and the new rules. And I was terrified.

Which app do I use?

Do I need to be on more than one app?

How long am I supposed to wait before I have sex with someone?

Do I need to buy condoms now?

Is there still the 3 date rule?

Which app do I use?

Am I supposed to go for coffee first or drinks?

What day of the week am I supposed to use for the first date?

When do I move to weekend dates?

Do I date someone with kids or without kids? Do I care?

Do I have to tell people immediately I am divorced, oh wait, I am not even divorced….

When do you decide to take the conversation outside the app?

Is old school dating dead?

How do I go out to a bar now? All of my friends are married?

As I started to go out on dates. I found the hardest part to get over was “the divorce stigma.” This was my biggest fear. But one I realize now was all in my head. I was so paranoid about telling people I was divorced. That it would mean I was damaged goods. But after finally getting out there and actually having the conversations, I soon learned that for some people it was a problem, and some people it wasn’t. And if it was, it simply meant this person is not for me.

I am awesome. Shit happens and life happens. And sometimes it’s for the best.

LESSON 2: It’s ok to be divorced. It’s not a reflection of a bad relationship and anyone who sees it that way – well – you shouldn’t be dating them.

After finally getting into the groove of dating again, the third big lesson I learned from dating in my 40s was to be clear about what you are looking for and what you need.

Dating in your 40s is not as carefree as your 20s. Your vantage point has shifted. Your time is limited. Your more mature. Your goals are different. You know who you are. And you should approach every date as such.

I always say to the man I am dating now, I am so glad I didn’t meet you right after I separated, cause we wouldn’t be together now. I wouldn’t have been emotionally ready. And I wasn’t looking for a relationship then, I was looking for a transition.

I read a quote that after a breakup, the loyal one stays single and deals with the damages. The other one is already in another relationship. It couldn’t ring more true.

To be brutally honest, as I always am on this platform, the first thing I had to prove to myself after separating was simply that I could date again and feel confident and comfortable with it.

I hadn’t so much as kissed another male for 15 years. And the thought of physically being with someone else was so scary. I needed to get over the shock and drama of my separation and divorce. I needed to break the dating seal. And to be honest, no matter who I met, it wouldn’t have been the right time. I wasn’t looking for anything more than that.

Mt friend Bobbi Brown wrote me an amazing simple email. “First of all. You’re hot. And smart and nice. Got to get you over the hump. And find a 30 year old surfer. For a weekend. ” You were right Bobbi, that is what I needed. That’s why you are JustBobbi.

People may be looking for anything from companionship to casual hookups. Some men are looking to get married and have more children.  And in your 40s and older, you have to balance dating goals with your career goals, different kinds of financial responsibilities, families, children and living situations. It’s more complex.

Once you hit your 40s, you’ve likely you had a major relationship, whether marriage or long-term partner—and, if you are dating in your age group (another story on that), the person you’re dating probably has, too. You want to make sure you have processed these relationships and know what you want out of the next one.

LESSON 3: If date 2 goes well, have a “real conversation” early. Be clear about what you want out of the relationship and what they want. Don’t waste anyone’s time.

So I made it into the digital dating scene. It was weird to say the least. Meeting random guys for drinks and coffees throughout New York City. I couldn’t wrap my head around it. Enter lesson #4…

LESSON 4: Disseminate the “I’m single” message and do it like this…

I was still going through the “divorce stigma” and it was uncomfortable telling people about it. How do I do this? Do you send a group email? A group text? A note to each of my friends personally? Announce it with an Instagram post? Then, if I do that, I have to get a bunch of “I am so sorry” notes back. Ugh.

Until writing this piece on Charlotte’s Book – I only told people I was divorced as it made sense. If it came up in conversation and I had to talk about it. In hindsight, it would have actually been better to be more open about it earlier. To yell it from the rooftops. However uncomfortable that would have been for me…and maybe them. The first person I sat down with and had a real heart to heart to heart was my friend Michele. She made me feel normal and told me story after story of similar situations.

Had I done this sooner, I would have had more support. And, as it relates to dating, if you don’t want to only rely on dating apps, you need to disseminate the message to your community. Because after all the apps and random meetings, I actually met my current boyfriend the truly old school way, through a friend of a friend of a friend. And here’s why:

I finally felt confident enough to let people know what I was going through. I started arranging one on one coffees and breakfasts with each of my friends and some of my old colleagues that I was still close with. If they weren’t local, I set up a call. I took the time to let them know what I was going through. And what had happened. It was so much more personal than an email or a text or a post, and it allowed me to reconnect with so many of my community that I may have lost touch with through my 15 years of marriage. It happens to the best of us.

This allowed me to not only have real personal conversations but let me reconnect. I also learned through this process who my real friends were. I created a renewed community of support that I am grateful to have now. I learned which people really showed up and I reconnected with people whom have now become the dearest of friends. Friendships, just like relationships, change from your 20s, 30s and 40s. You know what I mean.

And just like relationships, in friendships, if people don’t know what you are going through and what you need, they can’t help. So, set up after set up after set up after set up later, I met someone. And he is the most awesome human being alive. It took quite a journey to get here (for both of us). So far so great. So amazing.

This brings me to my last lesson: dating is not like the Bravo show, Girlfriends Guide to Divorce. I freaking love you Lisa Edelstein, but that show is just not a real representation.

LESSON 5: You are not living in a Disney movie! Expect to cringe. Embrace the cringiness of it all. It’s not supposed to be feel uncomfortable. Lean in. If you are comfortable, you are probably not doing it right.

Photo credit: The 1998 American romantic comedy-drama film staring Angela Bassett, Taye Diggs (in his film debut no less!), Whoopi Goldberg, and Regina King. If you have not seen it, you should watch it tonight.

Want more relationship stories? Read my follow up on divorce learnings, and a man’s POV on the 15 year itch.

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