Trying too hard
I recently went on a pseudo-date with someone I was really interested in. I say pseudo-date because it was more of a mutual friend who I was attracted to and whom I knew was single and the date itself wasn't official. We were both invited to a dinner of many friends to celebrate one mutual friend. And while I think it went OK – They followed me back on Instagram and exchanged numbers with me – I felt super off of my game.
I think there were a lot of external factors at play in the situation… but plenty of internal ones too that made for an uneasy exit when it all wrapped up.
Working with the situation
To start, this was a mutual friend of a close friend of mine, so it was going to be a warm introduction over a fun and flavorful night of drinks and a long dinner. I had a bit of background going into the evening on this guy and everyone else attending knew that I was interested in him.
Him and I are very similar people – we’re interested in the same things with similar hobbies and careers, and similar backgrounds, so it was hopefully going to be an effortless night.
The only thing I really wanted to get out of the night was his contact info and a connection, and while I did get that (probably out of courtesy more so than attraction) I couldn’t help but feel that perhaps this was a missed opportunity for something a bit more. Maybe I was being too critical of myself – maybe too unrealistic for a specific dreamy outcome of the evening – or maybe I got all of what I could and it was the best outcome.
Coming home from that evening I felt that I didn’t bring my A-game, and not just in my head but my whole body. I was sweaty, nervous, and shy as I overthought every word and decision I made sitting at the table trying to calculate my way to making a connection winning him over. It didn’t help that I was surrounded by friends who knew that I was interested in this guy – My dating self is different than my friends self. Going into this situation I had accepted the terms though: it was going to be a night with friends and a warm intro.
We go into every situation with our own set of tools to use: Nice clothes, great cologne, an accessory here or there, a pre-date workout, a couple of signature one-liners that always hit, and our repertoire of interests we’ve accumulated.
Alongside these tools we also have our lessons-learned from old dates: When to do something, when to say the right words, whether to order another round or let the current one stretch, how to make someone feel open and conversational or how to flirt.
The combination of tools and lessons need to be in parallel to make for a winning blend, but more importantly I think we need to be in the right mindset.
The reason why I wanted to write out my thoughts on this experience is because even when I felt that I had so much in common with this guy, I felt like I failed to 1) indicate my interest and 2) be my most authentic self in the moment. I also want to decide for myself how I’d like to continue this friendship and help design a mindset for myself to keep it alive.
Hey, I’m interested
It’s hard to know how to put the gas pedal down to show interest in someone. I think there’s a natural magnetism that happens with attraction where body language does most of the communication. For example, I once attended an "Anything But Clothing" party where I wore minimal clothing (as one does). At this party, I noticed that people would occasionally look at me or quickly look away when I made eye contact. It's natural to stare when we feel attracted to someone.
One type of body language that’s been extremely consistent is when someone touches their neck – it’s generally a sign of discomfort or anxiety in a situation. That’s something that happened a lot in the early part of the night with this guy, I think he was a little bit less integrated into the friend group and may have felt a little nervous despite seeming to act relaxed and outgoing.
In this scenario two things seemed to happen throughout the night: I didn’t catch many glimpses from him and he touched his neck a lot.
I’m not someone to assert myself over someone or put them in an awkward situation, so I felt that it wasn’t appropriate to make any moves or stir any deep topics that may make him feel uncomfortable. While I can be an intense person, it didn’t feel like the right invitation to do that.
But with all of my hesitancy, I still felt that there were ways I could have better expressed myself to have it be abundantly clear that I was interested in him.
How though? I could have made better eye contact, holding my gaze for a bit longer. I could have surfaced topics we both would enjoy better. I could have sought more one-on-one time while we were transitioning from the bar to the restaurant. I could have used my proximity to get a light shoulder tap in or leaned in a bit deeper to the conversation. I felt that I could have been more memorable by being more vulnerable, beginning topics of conversation that would have helped form a deeper connection besides surface conversation.
Being my authentic self
Before the "pseudo-date," I had built up a lot of expectations for the evening and wanted to be at my best. I spent time choosing the perfect outfit, including a nice shirt and a jacket, and I even trimmed my hair and chose a specific cologne. The subtlest decision, however, really stressed me out: I didn't want to appear too nerdy, so I left my Apple Watch at home and wore a single gold chain instead. When he complimented my gold chain, I nervously explained that I usually also wear an Apple Watch but felt that it was a bit too obviously "techy." He responded, "Oh, I just own that I'm techy." This was a bit of a bombshell for me.
Looking back, I think I psyched myself up too much and ended up making myself more nervous and unlike my authentic self. I could have easily worn my usual casual clothes and been more relaxed, cool, and confident. After all, he wore an oversized Lululemon shirt and seemed completely comfortable despite us being at a nicer restaurant. I think that trying to impress him by wearing something I don't usually wear messed up the chemistry and security of my decision-making. As a result, everything felt a bit rocky and I struggled to focus on the moment and enjoy the evening.
Rationally the emphasis of the evening was on another friend, and it wasn’t just a casual hang out. If I went into the evening with an attitude towards it being a friends night rather than a pseudo-date, I would have likely acted differently… more myself. That wouldn’t have been the worst if it was just a normal date either!
Keep the flame alive
With all of my anxiety of the night, I think it’s still a good sign that I got both his number and Instagram. That at least keeps the door open to future contact. But, I feel like I failed to indicate that I was interested in more than just keeping in touch. If we were on a scale of 1-10 with 10 being deeply connected, I feel like we only really made it to 2 when I was hoping we would have graduated to a 4.
I feel like there are two approaches here: I could either go all-in and straight up ask him on a date over text, or I could extend the relationship out for a bit of time to nurture a longer-term, friendly connection.
From the read on the situation, it seemed like the first option would be a bit too much, even aggressive. Nobody wants to get hit with a weird message from a friend of a friend implying there was something that wasn’t really quite there. The second option sounds a little too passive. While social media is good for resurrecting friendships with shared interests, relying on him to post a story that I could comment on that doesn’t feel weird doesn’t feel like a winning strategy.
I think I’m going to text him soon though with a link or something related to what we were discussing. That feels proactive enough but not intimidating. Perhaps a “Have you heard about this?” or a rehash of something we had chatted about. Maybe a link to my gold bracelet that he complimented.
It doesn’t feel great to have to overthink this next interaction, but it is pretty important if you consider how to keep something alive. The good part though is that I feel that I have been in situations like this before where I’ve taught myself that it’s ok if something like this fizzles out. While I’ve written about how social media can be painful to hold on to for the connections we’ve made, something gives me a bit of hope that the interests we share can find a way to intersect.
Was the date the ideal setup? No. I definitely learned not to treat casual friend hangs as first dates. A first date really must be between two people – unobstructed by the expectations of others. I also learned that it will likely backfire if I over-calculate a situation. Being relaxed, calm, and confident are much more valuable than trying to project myself too intensely.
Conquering my insecurities starts with facing them as my true self with the tools and lessons I feel most comfortable with.
Thanks for reading again – I’m starting to feel like I’m getting in the flow of things on this weekly cadence.
If any of this resonated with you I’d be infinitely grateful if you’d share this with your friends!