To set some expectations right off the bat… I’m not sure this piece is going to be anything but a bunch of my recent thoughts on dating and love. I typically try to write with purpose and to provide lessons, but this time around is just going to be an open conversation with myself. Hope you enjoy.

I recently had someone come into my life that took me completely by surprise. As one who is still figuring out the next chapter of their career and arguably life, I wasn’t exactly looking to date anybody or consider someone for the girlfriend role. My priority was and still is trying to figure out that next career move that not only makes sense for me, but is going to make me happy. It’s also been writing more and working on my book. So when a certain woman messaged me on LinkedIn and we took the chat to iMessage, I thought it was going to be another consulting session. Fairly quickly the texts escalated to being flirty, and within a week we were talking almost daily. On top of that, we went on our first date to L’Antica Pizzeria da Michele and I don’t want to speak on her behalf but I had an incredible night of laughs and getting to know each other on a deeper level. It was arguably one of the best first dates I’ve had in my life. I do want to give a disclaimer that despite enjoying my engagements with her, I was still hesitant to let it bloom into anything past the surface because of the uncertainty going on in my life. I made some of these hesitations known to her, and she also told me that she wasn’t actively looking to date someone but also didn’t want to let someone good just pass her by because of everything else that life was throwing at us. I slowly started to warm up to the idea that this was an individual who not only I enjoyed being with, but might be a big part of the future that I am building. Despite me being unemployed and not having that ‘much’ to offer on paper at the moment, she was extremely supportive. She congratulated me when I got my first set of job rejections because there was better things coming. She reminded me to stay positive and to keep looking forward. It was the first time in a while that I’ve had a woman be supportive of me, and in a sense, ‘chase’ me instead of me putting in the majority of the effort to attract someone. She was always texting me and calling me to let me know that she was thinking of me, and we’d talk about whatever was going on in those moments. It was refreshing and something that I really appreciated given the lack of stability in other facets of my life. We still had a lot of getting to know each other to do, but I felt really good about this woman and the potential we had together.

Just as quickly as she entered my life, she’s almost seemed to have left. A few weeks ago, there was a week where I am sure it was a roller coaster for her. Early in the week she secured her first round of VC funding for her company which I was incredibly proud of her for doing. She also had a lot going on with dropping off influencer gifting packages, managing a two day pop up at the Grove, and some sudden family priorities. This was the first week that our communications dwindled fairly quickly, and we went a few days without speaking. I brought two friends to try and visit her at the pop up and show some support, but I guess I missed her because she had left by the time we arrived. This was causing me a bit of anxiety because prior to this, she had originally asked me to do something for Valentine’s Day in which I countered that it was a day of mourning for my Nana and I didn’t want to do anything. After some thinking, I realized that I can’t keep using that excuse if someone is important to me. I need to show up for that person since they are still present in my life and not dwell on my Nana who is gone. That’s when the planning started to do a romantic surprise for her.

In one of our conversations, she mentioned that she loves Scopa Italian Roots but really wanted to try Felix Trattoria in Venice. If you’re not from LA, then Felix is a pretty difficult restaurant to get reservations to as it’s always booked out weeks in advance. I proceeded to keep the OpenTable app open on my phone and checked every hour for days until I was able to secure a reservation for the Sunday night at 7:30pm that had opened up suddenly. I was excited to surprise her with this, not only because she had been dying to try it, but because I wanted to show her that she was important to me even if I hadn’t been saying it as much as she had been. The problem was, we hadn’t talked in over 3 days at this point and I didn’t know what her availability was. She finally got back to me and told me that she couldn’t make it and had a lot going on, but would call me in the next day or so to explain and catch me up on her life. Unfortunately, that call never came, and we proceeded to go another few days of silence before I had replied to one of her IG stories. She apologized for being distant and said that work and her personal life had consumed her, so I tried to remind her that I was here for her in whatever capacity she needed. We would go another week and a half with no interaction until last week when she had replied to one of my stories about writing the book. I took the opportunity to try and turn that into a conversation about what was going on, and she reiterated that she had been pretty overwhelmed the past few weeks with both work and personal life. She mentioned that she had been fairly introverted and doing a lot of self-reflecting but was appreciative of this time to really learn more about herself. She then asked me how I was doing and I replied but then got no answer. Ghosted again.

This has been a confusing experience for me because while I want to respect that she has a lot going on in her life and being introverted has helped her cope with it, I have also seen her posting IG stories with other guys as well as seen her profile active on Bumble which sends me an entirely different message. Granted, we are not together and both of us are free to do what we please, but I can’t understand how we went from almost a month of talking daily and discussing future plans together to radio silence other than the occasional IG DM to keep the door open. There wasn’t a fight. There wasn’t anything negative between us. It would be easier for me to process if we had a falling out and realized that we both didn’t like each other… but it’s kind of the opposite. Our last text messages were full of laughs and positivity. Our last call was actually making plans for later in the week to see each other. It really makes no sense to me.

For some, this wouldn’t have affected them too much. Yes, it would suck, but people come and go and it wasn’t THAT much of a time investment so they wouldn’t care. I came to the realization that something within me always desires to know why things happen. I need to know the answer to things constantly. I am always asking in-depth questions to get to the bottom of situations. This curiosity has helped me immensely in my career but has arguably made dating a nightmare at times because of how much I overthink the situation and start to come up with my own answers to the ‘why’ a person acts the way they do. In this case, I started to think about the worst-case scenario that she has been talking to other guys and found them more interesting, so she didn’t bother giving me her time anymore. I’ve experienced in the past where a girl will keep me on their roster but not actively pursue me, and this is starting to feel that way. It’s also made moving on even more difficult for me because I put much more importance on the situation than it probably deserved. In reality, I’ve known her less than 2 months so she shouldn’t really be impacting me the way she has been and honestly, this probably wouldn’t bother me if my life situation was a bit more normal. I’ve had pretty quick relationships in the past and I’ve never let them get me too down or dwell on them. This time around though, there’s a lot of other uncertainty in my life given my career & immigration status, so I think it’s multiplying the power of the feelings I am having.

I write all of that to give you an idea of how much relationships mean to me when I decide to take the plunge and actually try – regardless of the amount of time that has passed. I’ll admit that I have been in a lot of casual relationships where I was probably called a fuckboy by them at some point because of my lack of commitment… but at the end of the day, I really am searching for someone to build an empire with. I try to be honest about my intentions and whether I am actually looking to be serious with the person, but I still find myself in situations with women where we’re sleeping together and I don’t really move past that. It takes a lot for me to make the decision to commit to somebody. I am afraid of rejection. I am afraid of losing them. I am afraid of being alone. Taking a leap of faith in someone is a difficult thing to do when these fears are front and present in your mind, especially after a bunch of failed relationships.

I’m currently 32 and have been single the majority of my life, so I’d say that I am ready to move into that next stage of dating someone with substance. I’m not saying that I need to go and get married tomorrow, but I’d love to find someone consistently to talk to, hang out with, and lay the foundation for what might be something very special. I know women think that guys don’t have emotions and we don’t care about being ghosted or being rejected, but I can say for myself that it hurts a lot. I question myself and what I have to offer, as well as what I am ‘missing’ compared to other guys out there who seem to have nothing but success with dating. Rationally I know that this isn’t the way to reflect on my relationships, but it’s hard not to compare yourself to others when you see the fantasy world of social media making everybody look better than how you feel. It’s something that I am working on still.

I’m a bit of a hopeless romantic when it comes to dating because I was told my entire life that I wasn’t allowed to have a girlfriend. I also looked to both my Mom and my Nana who had horrible relationships and vowed to have something completely different. I want to be there for my partner, and be their biggest fan. I want to show up for them every single day that we make a decision to be together, no matter what may be happening in our worlds. I’ve done a lot of things on my own in my life, and I’ve recently realized that I would love to share them with someone else as much as I want them to share their life with me. Unfortunately, it hasn’t really worked in my favour. I also think my expectations might be a little biased because most of my reference points of successful relationships are the ones I am seeing on social media and we all know how those aren’t telling the full story. Although, I do think that loving someone can be easy when you know it’s right.

In the meantime, there really isn’t much that someone can do in this situation other than to keep putting themselves first. As much as I’ve been hurt over the past few weeks, I still have made sure to prioritize doing what is important to me and brings me happiness. Every day hasn’t been easy, but at least I can say that I am choosing myself each day.