I started dating: hilarious stories from the trenches

Hello, Gorgeous! 

I started dating. 

Eligible suitors are everywhere as I have Jewish friends who are born into the culture of introducing endless connections Jewish or not. It is a gift to create relationships and potentially more lives. God is happy when you help two people fall in love. 

This is extraordinary as everyone I know happens to be someone. 

Because of this, I am a lucky girl. I built my circle with intention and spent time and energy where I met others who do the same. 

Knowing a few good people is not enough. I had to meet more new people. This is easy, because I go out several times a week. Yet I still needed help. I only have so much energy and time talking to make acquaintances in one night.

I applied to join a dating app that was heavily vetted before being accepted. 

Despising online dating, I had to open up my sphere of community. This was not my first choice, but I do not want to be tied to only seeing men I naturally cross paths with, because everyone I know is a woman. Or does not speak English where I circulate. 

If I want to date a real estate guy, I would play tennis. If I want to meet a lawyer, I would go to my local synagogue. If I wanted to meet a doctor, I would faint at the synagogue. In addition, I am not only interested in dating Jewish men. 

Online dating is so weird, because it feels unnatural. There are also a lot of weirdos on the internet (including me) and immature guys who never built social skills so they lean heavily on apps. 

This is why I prefer meeting people in person or on an app where exclusively cultivated members can be selectively chosen. 

I do not play with people’s hearts or bodies. 

At 31, I have grown and the dating pool has actually opened up more than ever. Having lived a bit, knowing how to present myself gently, and being fearless really helps. 

Now I am looking for love. Not dates where I lose interest after a couple of months. People are not disposable and should be treated with silk gloves. 

They take the effort to make a space for you in their lives. To put their best foot forward for what could be a very long time of sharing everything with you. 

I used to be a sucker for grand gestures and passionate declarations of infatuation. 

This time I want to get to know someone. Be careful and clear with my words and actions. 

I want to find someone I can sit in silence with even if we are in the same room for hours. And still feel their love, their warm spirit towards me, and affection through casual glances. 

Not needing to fill the silence. I want years of side by side where we do not feel tense and can simply breathe. Wouldn’t that be lovely?  

These first few weeks of dating were interesting.

I did not cast out a wide net at first, but the men started pouring in. Surprised at how some of them threw themselves at me–and tasks around my home–they wanted to help me genuinely build something and be there.

Romantic as it sounds, I reached the point of having found gentlemen who wanted to show up making a strong first impression. Pleased, I turned down their efforts only to be met with a man who naturally inspired me to stop all contact with the rest of them.

Here are the weird interactions before I found him. 

My first date that didn’t happen: The boy who didn’t know who he was

At first the app felt slow, because people wanted to chat forever. The real men who acted right away immediately stood out, because they asked me out after a couple texts. 

This man did not. 

In every photo, this person looked completely different. Each expression on this man’s face was uniquely its own. As a joke, I told him, You don’t even know who you are.

He laughed and left a voice message that lasted over 1 minute. Each voice message he sent subsequently was over 1 minute. There was a lot of back and forth as I was getting my bearings in, because I have not been on a dating app in years (Thank God). 

Finally prompting him to be direct and ask me out, he did! Hallelujah. We agreed 10pm. My schedule is nocturnal and I meant for this date to be short.

He wanted to meet at a bar even though it says I do not drink on my profile. 

Mkay. I can have a mocktail or sparkling water. Not a big deal. If I feel safe, perhaps I can have alcohol in future. We both planned on ordering Waymo cars to get there.

As I got in the Waymo I already scheduled, I started the ride. Right when I started the ride and the car began moving he texted.

Him: Are we still on for tonight?

MY HEART DROPPED. 

I almost fainted and banged on the door to let me out. 

We agreed 10pm.

I was 10 minutes away from the bar and he lived farther, so he should have been either on the way or there ALREADY. I have never panicked so much in my life.

Texting my dear friend Mia, she said stop the car and turn around. Go home. I did not want to be rude and stand him up.

Standing in front of the bar in a tiny dress and heels, cars flew by and I was freezing. 

Strange men passed me by and I could NOT tell who was a hipster or homeless. 

This bar was not my vibe. The music was overpowering rock, crowded with people, and there was a lovely French restaurant with white tablecloths and fresh flowers where I could hear my date when he spoke. I was there to get to know him.

Mia FaceTimed me to scream and laugh sense into me like a spy with an earpiece. 

She asked a question I would never forget: What would you tell me to do?

I would tell her to do exactly what she was telling me – to go home and laugh about it. This man did exactly what I prompted him to do and he even encouraged it, because he said he had not gone out in weeks. 

I did not want to turn this date into a horror story where he would be angry at future girls online taking it out on them. We already fear these men even if they are not serial killers!

She was already on FaceTime and he made me wait 20 minutes in the cold. Being a steadfast friend, she stayed on the line to guide me saying she could act sick/upset. With no time to splash Evian on her face to feign tears, she covered her face and said to say she’s not feeling well.

He catfished me. 

Sounding like Courage the Cowardly Dog, I saw him. Not really looking like his photos and lying about his height. I had no problem ditching this person, because he unfortunately deceived me. 

I was disappointed and pointed at Mia on the phone with her hand on her face saying my friend needs me in a panic. I was almost screaming in panic as I was trying so hard not to actually cry. Or laugh. 

Running out of there, I headed home and Mia and I laughed and felt terrible. She justified how he did me wrong on so many levels. Now we have a hilarious story to tell at each other’s weddings. 

The boy who texted too much

An Arab originally born and raised in Switzerland was highly interested in me. During the potential date aforementioned, he was texting me the entire time. Full blown Arab love bombing level.

I am talking 13 texts in a row with 7 inches of his messages covering my phone. Because I put my phone down for a few seconds.

He kept going back and forth asking for photos. I told him he can just look at my Instagram. He persisted. Confused, I was wondering if he was asking for nudes. He said no, normal photos.

Getting fed up with him not asking me on a date, I called him to not go back and forth texting on my phone like a 16 year old with their first phone. 

I want to actually talk to a real person, touch them, flirt, see them react. Not build a fantasy in my head. 

Me: Why don’t you ask me on a date?

Him: Why would I ask you on a date? I DON’T EVEN KNOW YOU.

Me: Isn’t that the point of dating? Getting to know someone? You go on a dating app not to date?

Block. 

The guy who sang to me

This gentleman was kind and lovely and asked me out on a lovely date, but it did not fit my schedule. In the interim, we FaceTimed and he sang to me.

Have you ever had a grown man sing to you? I have.

Not making any note about his voice, I immediately shared how I loved The Beatles as well. I was about to change the subject when he continued. I stayed on that call too long. 

After a while of not texting him, he asked me out again, and I told him how I met someone and wanted to take him seriously. He was kind. 

God bless him. I sincerely hope he finds someone who loves his dulcet tones. 

The boring orthopedic surgeon 

All of the surgeons I know are the craziest people with the fullest lives. They have endless stories on the life they have lived from my personal experience. 

This guy was really boring. All he had was his career to flex and you could feel it. Please get hobbies. I know med school is a lot, but why are you the only orthopedic surgeon I know who works, goes to the gym, then goes home?

You have enough resources to dive into eccentric hobbies and have a palette for food nobody else can experience. Why am I younger with more of a life and stories than you? I stopped talking to him. 

Also, I genuinely feel bad. It was so hard having to carry every dialogue on my shoulders. Been there. Done that. Don’t want it again please.

The boy who locked me in his car

This was a genuinely cool man I could see myself with. He was easygoing, had a life, dreams similar to mine, and we naturally had a lot in common. 

I could talk to him for hours. I did. Then I was locked in his car.

He brought me fresh flowers already in a vase and water – impeccable manners, picked me up, and took me on the loveliest date where we had the best scallops I have tasted in a long time. 

Then, he wanted to come back to my place. Gently massaging the notion away, he insisted. 

I told him about my strong, angry boxer ex who beat me up and is very scary. Stating how he could show up at any time – this was usually the day he would manifest at my front door. Trying to take off my dress, he groped me and I did not dare touch him. 

Almost to the point of begging, I told him to please drive me home safely and assured him I was looking forward to texting him later. If he did not do this, I would have gone on a second date.  

The gentleman who laughed at all my stories and gave me hope

The final man – thus far – is slow and steady wins the race. We had a wonderful first date and an even better second date.

On our first encounter, we exchanged dating app stories and I felt like he was going on. I apologised for rambling. He smiled, ‘Go on. I love seeing you animated.’ 

I don’t know if it was his French accent. I don’t know if it was his healthy high standards. Or if it was because we organically had so much in common. 

But I finally met someone I could be myself with and not scare him away. 

The lesson hidden in every bad date 

Dating has reminded me that the right connection does not arrive through grand gestures, but through consistency, ease, and genuine curiosity about one another. 

While these stories gave me plenty to laugh about, they also helped me become clearer about what I want, what I deserve, and what I am no longer willing to accept. 

Whether this journey leads to the Frenchman or someone I have yet to meet, I am content knowing that love is worth waiting for when it feels calm, mutual, and real. ♥️

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