I Went On A Really Great First Date And This Is Why It Backfired

I was really surprised by this match. He definitely didn’t look like my type, but there was one thing in his profile that made me freeze (in a good way). 

In one of his prompts he mentioned that his goal was to be able to cook a recipe out of the Snoop Dogg cookbook. My kids had bought me the same cookbook years ago and I don’t know a single person that has it. It also turned out that we had both cooked only one recipe from the book (the Orange Chicken). 

The other thing to know is that I love hip-hop. It is actually one of my must-haves. It feels a little weird to say that but going to hip-hop music festivals is something that I must have from a partner. Because these festivals are such shit shows I would never want to have to drag somebody to one of these events.

The other thing that made me really like him was his opening message. He had taken the time to notice that I like hip-hop and commented that I would probably like his playlist. I was intrigued. He also told me that he had been to the Travis Scott concert twice and to another concert by A$AP Rocky. Though I wasn’t all that physically attracted to his pictures, there was a lot here and I wanted to know more.

The texting itself was really easy because we had so much in common. After a few back-and-forths I decided that this was a person I really wanted to meet. So I went ahead and asked him out. He agreed enthusiastically and we exchanged numbers.

Our date was set. We would meet after my dinner with a friend. In retrospect, this was a bad idea because it put a lot of pressure on the dinner itself. Also, the timing was a little bit off because the dinner with my friend went later than planned

I didn’t want to text during the meal and I also didn’t want to tell my friend that I had a second set of plans. I wanted to give her my full attention. I also didn’t want to check my phone at the table, so I went to the bathroom and saw that he had texted me a few times asking for my estimated time. I texted him that I was running late. He said “That’s okay! I’m actually parked right outside the restaurant.”

I looked up and I saw a pretty fancy car. I was impressed, but I was also uncomfortable because in this environment I’m not that comfortable being in a vehicle with somebody that I don’t know or hasn’t been tested. 

The meal ended and I walked over to the car, he came out with a mask on and I decided what the heck just go with it. It felt so romantic, like I was being swept off my feet. I wanted to be in the moment. 

When he got in the car he took his mask off and I kept mine on. It was awkward that he didn’t ask me if I was comfortable or not. But again I let it go. He was excited because he had booked a spot on one of the rooftops and I thought it was really sweet that he had been so thoughtful about our date. He was obviously really excited to meet me which was also very refreshing.

We got to the venue, but because my dinner ran too late, it was closing. He said, “Don’t worry, I have a backup plan,” and pulled out a cooler complete with glasses, gin, tonic, lime and also a mini bottle of champagne. We drove to a park like a couple of teenagers and drank and talked in the car. 

The conversation flowed really easily. It turned out that we had a lot of common interests even in addition to music. For example we both knew way too much about the Kardashians. That’s something that I’m usually kind of embarrassed about LOL.

But the date went on an hour longer than I normally allow. After having worked all day and having dinner with my friend I was tired of talking. Also my teenage kids were home. It didn’t really matter because they can take care of themselves, but because I only have them 50% of the time I really just like to be there for them.

So he drove me home and before I got out of the car he gave me a box of cupcakes to give to the kids. I thought that was really sweet! We did not hug or kiss goodnight because I don’t do that right now especially in this environment with Corona, but it was still a warm goodbye.

I hadn't felt this way for a long time after a first date. As a Dating Coach and a very experienced dater, I usually know how to stay cool. But it had been such a long time since I’d been on such a romantic date. He was also totally age-appropriate and had kids so it was one of those scenarios where I could see how it could move forward and that excited me. But it also made me feel really nervous. I wasn’t sure why.

When I woke up the next morning at 9 AM I got a text from him. I could already feel myself getting a little uncomfortable and I couldn’t figure out why. Upon further reflection, I realized that all of his grand gestures, while nice, had made me feel like I had to reciprocate. And I wasn’t ready to do that. Also I realized that I had broken my own rule of not spending time with someone in an enclosed place. I had gotten caught up in the moment. I don’t blame him for wanting to share this moment with me or for forgetting to ask for my permission on the being inside portion. However it just made me uncomfortable and of course my mind went to the possibility that I had contracted Corona. Dating in these times is very, very strange.

I paused on texting him back. One, because I didn’t have time to get in a conversation. And two, I didn’t really know how I felt. I didn’t wanna start a pace that felt really fast. I recognized that in this situation it could quickly turn into a relationship without my actually deciding that that was what I wanted. So I didn’t reply until later that evening. When I did reply, it was kind of short. It was nice because I definitely liked him but I wanted to slow down the pace and thereby slow down the expectation.

I think he’s good at reading cues. He didn’t reply that night and that actually created some tension but in a good way. I lay in bed wondering if I should’ve texted him back. Maybe he thought that I didn’t like him. It made me want to hear from him whereas before I was actually kind of dreading it. 

It’s really funny how timing and nuance can change the way that we feel about somebody. Sometimes people call this playing games but I don’t really see it that way. I think that pacing says a lot. He was paying attention and giving me a little space.

I heard from him late the next morning and this time, I was really happy to hear from him. So we went back-and-forth. It was pleasant.

Then my phone rang and his name came up. The anxiety kicked in. I actually just don’t like talking on the phone, and sometimes I avoid the phone because I can’t think of how I will get off the phone. It’s just a bad habit I guess. So I let the call go to voicemail and texted him that I would call him back. 

It turned out that he wanted to take me out for dinner that night. I would have gone because I like spontaneity, but because I’d already been out the night before, it just wasn’t going to work out this time. I didn’t call him back.

Following this exchange I actually got a vaccine appointment so I decided to quarantine until then. I told him that I would be free on a certain date. We will see what happens.

I do continue to reach out now and then to check in and to kind of stay on his mind and make sure that he knows that he’s on my mind. But I just don’t feel like texting him that much. I don’t know why.

I would definitely like to see him again but before our next date I will ask for him to get a PCR test because that’s important to me. Not everybody is comfortable with getting tested and that’s okay. I wouldn’t hold it against him but it’s just the rule that I want to maintain when I’m dating.

For the first time in my life, I find myself in the role of sporadic texter. That person who says they want to meet again, but doesn’t specify when. I finally understand what it’s like. Yes I like him. But despite those feelings, there’s no urgency. But I also don’t want to let it go entirely.

Additionally, I don’t really feel like dating. Honestly this has never happened to me before. I’m just really focused on work and having a blast. 

Being in this position is so interesting because I’m almost always on the other end. 

So the next time when I’m staring at my phone after a really amazing date, hopefully I’ll take it less personally. Just because somebody isn’t super consistent and/or sporadic, doesn’t mean they don’t like me, it just means other things are happening in their life at that moment. 

Giving the other person space can make a difference. And by keeping the door open, it may lead to a rekindling of sorts. You never know!

I am a Dating Coach and I help people navigate situations like this. I learn every day for my own personal life and from my clients. I would love to help you too. If you think it would help then please use the link in my Instagram bio to get in touch!