Column 4: Dating & What I’ve Learned So Far…
“There will be an answer, let it be.” - The Beatles
Wine: ONEHOPE 2018 Napa Valley Reserve Cabernet Sauvignon
Recipe: @cookingforone Goat Cheese Steak Salad
Well, it's been quite a ride. Dating in my 20’s has been anything but boring. While I think at the end of the day, we are all more alike than we are different, I think there are some elements of being gay that can add extra layers to & complicate relationships. That sentiment tees me up perfectly to the wine pairing for this column. Cabernet Sauvignon is incredibly flavorful, complex, and generally gets better with age. It's layered and opens up more and more as it sits in the glass. The first sip can often be very different from the last. Similar to a great cab, as I’ve gotten older, dating has gotten better and generally just more fun. The more I experience & learn, the more I am just trying to enjoy the ride. And hey, what’s better on a good date than a steak and a glass (or bottle) of cabernet?
PS - If you go out for a hot date & a steak, bring home the leftovers and make this bomb Goat Cheese & Steak Salad for lunch the next day. And if it was a bad date, then I highly recommend pairing it with another glass of cab.
Out of respect for the privacy of the men written about in this column, their names have been changed.
I was walking into my favorite dive bar, and at least 3-4 drinks in for the night. I was out for the evening with one of my friends, and life was good. I was beginning to spend less of my time and energy thinking about dating & relationships, and more just trying to have fun and enjoy life as things were starting to loosen up with the pandemic. It was one of those carefree nights where I was able to just be present and enjoy the simplicity and fun of getting my buzz on with a good friend.
I walked through the crowd of people along the long bar front, all trying to get their hands on their next cocktail. I was eagerly looking for any slight gap I could fit into to get our drinks. And then when I was about halfway down the bar, my eyes locked with a guy who I had dated a few months prior. “Fuck” I whispered under my breath. It was too late to turn around and act like I didn’t see him. This encounter was going to be inevitable. I had a bit of a bad taste in my mouth when it came to him, and didn’t really want to talk to him. I had spent the last few months trying to feel less hung up on him, and seeing him again brought back all the feelings I had thought I had already moved on from. Anyway, seeing him instantly put me in a bad mood, but I didn’t want him to know that. There's a Taylor Swift lyric where she said, “This is looking like a contest of who can act like they care less”, and in my mind, I was going to be cool as a cucumber and win this battle.
As we got closer and walked towards eachother, I gave a very quick & cool “hey”, me hoping that it exuded the most chill / non chalant / “I’m having the best night of my life and fuck you” vibes…ever. I used to overextend myself with guys, but those days were over…at least, that's what I was working on and telling myself. He said hi also, gave a little smirk, and I kept walking. As I got a few steps past him, he laughed and said “What, that's all I get?!” I took a deep breath, turned around, and said “yep” and continued over to the bar to get my cider. I vaguely remember him saying something like “Oh, come on, don’t be like that.” But like I said, I was trying to give very chill “fuck you” vibes, so I acted like I didn’t hear him and just kept on walking.
About an hour and a drink or two later I was at a pool table, still trying to shake off the feeling of being a little rattled. I was trying to ignore his presence, but it was hard. I sure as hell wasn’t going to try to talk to him, but sure enough, he strolled over. He was a little drunk, but pretty coherent. As we started talking, I wasn’t being particularly friendly and what ensued was a bit of bantering back and forth. I’m usually pretty friendly & outgoing and generally if I’m ever mean to someone, I usually feel guilty about it and apologize shortly thereafter. But I was feeling a little salty that night about how he had treated me months before, and didn’t feel like being overly warm to him. What was so interesting to me was how much more engaged in the conversation he was as I kept giving him attitude. I wasn’t being overly mean or malicious, but I was calling him out for what I saw to be his shortcomings when we dated. And the crazy thing was that I could swear that he liked it in some twisted way, and before I knew it, he grabbed a fistful of my shirt and pulled me into a kiss. And there we were, making out in the middle of Napa’s diviest bar. And thinking back to all of the nights of me drunk at bars trying to make out with a guy (and sometimes failing), the one time when I wanted nothing to do with a guy, it happened just like that. Funny how the universe works.
Like most singles, I of course debriefed this experience with my friends after, and to my surprise, their response was “Well yeah, duh. Of course he ended up making out with you.” And call me crazy or living under a rock for the past 30 years, but that was one of my first experiences of (accidentally) utilizing the laws of attraction, at their finest.
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By no means do I think that I’ve seen it all when it comes to dating & relationships, but I’ve definitely experienced a lot and kissed (more than enough of) my fair share of frogs. I thought alot about what my intention was with this piece. I asked myself if there was a key message I wanted to communicate. I am still finding my way as I date, and even in the darkest days or weirdest experiences, I just try to tell myself to simply keep going and try to enjoy the ride. One of my biggest intentions with Writing For Hope is to share my stories in the most raw and authentic way as I can. While I don’t necessarily have a key take away, there are some “golden nuggets” of things I’ve learned woven throughout these stories. And at the end of the day, I’m really just figuring it out as I go.
I’ve been through the good, bad & ugly while I’ve dated throughout my 20’s. I think I’ve felt almost every emotion possible from infatuation to anger to hurt to confusion to bliss. I’ve met people I saw a future with and there have been so many moments where I’ve felt completely lost and at a loss for why I keep “failing at love”. There's been moments when I genuinely wonder if I will end up alone for the rest of my life. I’ve wondered so many nights why I have to keep going through what I’m going through? Why so many people I know have found love so young, and why I keep striking out. I still am not sure, and a big part of me didn’t want to write this column right now, because when I began writing it, I didn’t really know how I would end it or even what my message would be. I still don’t have the answers to many of the questions I wrote above. But I know there is always hope, even if you can’t see it.
The following is by no means a comprehensive summary of my entire dating history, but some of the ones that were the most memorable (for a number of reasons), and include some of my best learnings from dating as a gay man.
So here we go…
The first time I ever kissed a dude was when I was 20, just a few months after I came out of the closet. It was back when I was studying abroad in Italy. I was on a weekend trip to Croatia, and I met him on our bus ride over from Florence. Skylar was an east coast college lacrosse player and a “tall drink of water” as far as I was concerned. Blonde hair, blue eyes, 6 foot something…the whole shebang. Before and after we met, there were a lot of stolen glances and lingering gazes back and forth between us. I remember walking around Split, Croatia with him one night after dinner, and after hours of flirting. We’d “accidentally” bump into each other as we walked down the street, and finally he put his arm around my waist. We trailed to the back of the group of friends we were walking with, and he finally pulled me behind a car, pushed me up against its trunk, and kissed me. I know some may want to barf when they read that because of how corny it sounds, but it really was that good. It was my first kiss ever with a guy and I remember thinking “Damn, 20 years in the closet, and that was definitely worth the wait.”
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When I came back from Italy, and returned to school for my junior year of college, the first guy I dated was Braden. One of my best friends knew him and set us up. With him I fell hard and I fell fast. He was a stereotypically good looking dude who was more of the tall, dark and handsome type. There is something to be said about the first person that you fall for. I wouldn’t be as foolish to call it a “first love”, but he was a “first…something”, and it meant something to me. While it wasn’t the deepest or most significant relationship I’ve ever had, it was the first time I had truly let myself have & express feelings for another guy.
I remember we were out one night with a group of my good friends, and the two of us held hands as we walked down the main drag of bars in our college town. For me, at that time, that was a big deal. Especially after spending the past 20 years of my life in the closet. Back then, and still to a certain degree these days too, I was working through some internalized homophobia and struggle with PDA. I remember my heart racing when he grabbed my hand. My first feelings were of brief panic, wondering if people would stare at us. I tried to not think about what was happening around me, and to just enjoy the moment of affection with him. A group of guys walked past us, and I heard some muffled laughter as we walked past each other. One of them had said something, but I couldn’t hear exactly what he said. But one of my friends did and she spun around on a dime and said something like “If you ever say that again to my friend, I will fuck you up!” I laugh as I write that last sentence because she is a complete fireball. I was lucky to have her in my corner at that moment. While I can’t say that was the most tactful rebuttal, it did mean a lot to me that my friends would go to bat for me.
A few minutes later another one of our friends told me that one of the guys had made a homophobic joke as we walked past. That was the first time I had experienced hate (on a rather small level) while being out of the closet. It's strange to me that people would mock something that in and of itself is pure, good and not hurting anyone.
With Braden, I don’t think he liked me as much as I liked him. He ended up breaking it off before it really materialized into any type of relationship. But I was hung up on him for a long time after it ended. Like I said, there is just something about your first.
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A few months later I met another guy, Tanner. We met on the 4th of July and it was sparks from the moment we met. We just totally clicked on so many levels. It wasn’t long after I met him though that I found out that he was in the same fraternity as Braden, and to make matters more complicated, his “little brother” in the house. For those not familiar with the greek system, that means their mentor of sorts, not their genetic sibling. For the record, I have yet to date 2 siblings. Since Braden was the one who broke it off, I didn’t think he’d necessarily care all that much that I was now dating one of his friends. But boy was I wrong, and what ensued was a year long drama fest. We were all young and less mature than we are today, and it got a little out of hand. At one point Braden stole Tanner’s phone, and texted me. He was pretending to be Tanner. It was a mess, and that was when I learned my lesson about dating 2 friends. Whoops.
Tanner and I were very on again, off again, but I think we genuinely really cared about each other. He was an early bird, and he used to wake up before me and go get me my favorite drink from Starbucks. For me, it's the little things in relationships that mean alot to me, and I still think back to how thoughtful he was. He was also incredibly smart & ambitious, and I found that very attractive. We always just had so much to talk about - between school, work, friends and family it just seemed like there was never a dull moment between us.
Although I liked him, I just couldn’t shake this feeling that he liked me more than I liked him, and that he just wasn’t “the one” for me. I was truly enjoying spending time with him, but I was scared to let it go further and have his feelings grow stronger for me, and I didn’t want to settle down into a relationship just yet. I ended things and don’t mean to sound dramatic when I say that I think I broke his heart. He was shocked and hurt. It's a shitty feeling to have to do that to someone, but the alternative for me was to lead him on and then have that conversation down the road. And I think then, things would be that much harder for both of us.
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The next guy I dated was Colby. He was super fun and a sweet guy. He was hot as hell too. Seriously the guy had a killer bod (just had to note that).
I once went with him to his fraternity's “house dance” as his date. In my early days of dating, I would get somewhat anxious about doing couple-y things like that with big groups. I think it was a combination of me not totally loving PDA + just not totally comfortable with my sexuality yet + still trying to shake off some internalized homophobia. Coming out is not a one-event thing and then it's over. For me it’s lasted for years, and this night was one case scenario where, in a way, I felt like I was coming out again. It was anxiety filled for both of us. Especially in a very stereotypically straight male environment like a fraternity. That being said, he had the coolest, kindest & most welcoming group of friends that made me feel so at ease that night. On some level, they probably knew that it was a big deal for both of us, and made the extra effort to make it feel normal for us, amongst a bunch of other mostly straight people & male / female couples that night.
All of the above aside, he got suppeerrr drunk that night and later told me it was because he was so nervous. Him getting that wasted added another layer of stress for me that night in having to take care of him. I felt a little abandoned when I wanted to have him as my rock during that experience. After all, we were going through that experience together. But anyway, it wasn’t that big of a deal and he felt really bad about it too.
It was a quick fling with Colby, but to make things more complicated, he then dated Tanner. And that was when I realized just how incestious gay dating could be, especially in a small college town. We were all in fraternities and I even worked with Tanner at one point. Again, complicated. You could say I was a little relieved when college was over and I could start fresh in a new town, ha!
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When I was living in San Diego after college, I once dated this guy lawyer, Parker. He lived in Los Angeles, but would work remotely and stay with his parents in San Diego a few days a week. We both grew up in San Diego and had gone to rival highschools, so we connected over that. This was a strange experience for a few reasons because it was the first time I had dated someone who was out of the closet, but still kind of had one foot still in there. I remember making plans one night with him to go to dinner, and him strangely canceling at the last minute. He sent me a text saying that he couldn’t make it because he wasn’t feeling well, and then after a few small probing questions, he admitted that he couldn’t bring himself to come. His reason being that, despite him being out of the closet, he was too ashamed to tell his parents that he was going on a date with another guy, but also said he was so close with them that he didn’t want to lie to them about where he was going. I remember I was leaving work, walking to my car when I received and read that text, and feeling the biggest range of emotions as I processed what he was saying. At first I was annoyed and hurt that he was flaking, then I was angry that he lied to me, then I felt bad for him when I realized how much he was struggling with this situation. And then I couldn’t help but wonder “How close can you be with your parents if you can’t even tell them you’re going on a date?”
Despite the situation above, I still liked him and was trying to make it work. Planning & time management was a challenge for him. We were constantly making plans that he was always changing. After seeing this pattern in him, one day I finally challenged him on the subject. I told him that it frustrated me how flakey he was, and that triggered him to fire back and tell me that I simply couldn’t understand the demands of his job as a lawyer because of my type of work (emphasis on the word “type”). He’d love to tell people that he was a lawyer, and definitely had a superiority complex about it. I’d like to note at this point that he was the guy who would want to text me all day, every day, but then talk about how busy he was and how he had to meet his minimum for “billable hours”, and then flake out on plans. I wanted to ask him if his clients knew that he spent half of those billable hours texting the guy he was dating, but I refrained. Anway, I bluntly replied that his job had nothing to do with it, and that he was just a poor planner and communicator. Aaannnddd that was the end of that “fling”, let's call it. It was then that I realized some of my “dating triggers”. Well, really it was kind of a 1-2 punch of poor planning + superiority complex that was the final nail in the coffin for me.
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I once dated an ex-model, turned porn star, turned gay male brothel owner in both San Francisco and New York, who left all that behind to work in wine here in Napa. Yes, you read that right. He said he got tired of paying off the SF & NYPD to keep them in business. I promise you I couldn’t make this stuff up if I tried.
It's a quite funny series of events actually. I met Simon on a dating app, and I remember sitting at a coffee shop one evening, messaging with him. He told me to swing by the wine bar he worked at. I immediately liked the idea of dating a guy that worked at a wine bar, for obvious reasons. So I put my book down, and walked over. I was reading Cork Dork by Bianca Bosker that day…and still to this day still haven’t finished it. But now is not the time to tell you all about my reading ADD.
I walked in and the room was empty. He was standing behind the bar and I immediately thought he was handsome and mysterious, but in a dark kind of way. He wore his hair slicked back with gel, and was wearing a silk collared shirt tucked into dark denim, with a lion's head belt. You read that right, a fucking lions head made out of metal. To top it off, he wore thick chains around his neck, and had a silver bracelet with a falcon on it. I knew from the moment I met him that this was not “the one”, but there was something that drew me to him. He interested me. I remember telling a friend all about him, and she referred to him as “Dark Falcon”. Even today we still call him that when we talk about him.
He offered me a glass of cabernet, and we got chatting. Before I knew it, he was making sly hints at how good he was in bed and “how much he could teach me”. It was borderline Christian Grey, and I wasn’t hating it. If almost anyone else would have said something like that, I would have laughed in their face and probably walked out of the door, but he said it with such sly confidence that you couldn’t help but wonder if what he was saying was true.
Throughout our little fling, I always felt like he was, to a certain extent, holding back and that there was something that he wasn't telling me. Like I said before, he had this mysterious ora. Hands down he’d have been a Slytherin (Harry Potter reference, IYKYK). It wasn’t until our 3rd or 4th date that he dropped the pornstar bomb. When I met him, he alluded to having a bit of a “dark past”, and always said that he’d seen things I’d probably never see in my lifetime. I would chuckle at him and tell him he’s full of crap. Until this date. He didn’t exactly tell me willingly, but he kept alluding to this past of his, saying that if I knew the truth about him, then I wouldn’t want to date him. At the end of the day, I really don’t care much about people's pasts, and the whole pornstar thing wasn’t the reason it didn’t work out. This next part is. He proceeded to tell me how certain he was that the illuminati was real. And that they are listening to us through our cell phones. By that point I was 3 gin & tonics deep and I felt like I walked into the matrix. After that, he said that when he was a model in New York, he used to party with J Lo. Not sure how true that was. He then went on this rant about how he would have been a pro basketball player if he hadn’t been kicked off of his high school team because he came out of the closet. That part, I truly felt bad for him about. But he got kind of “braggy” about the whole being good at basketball thing, and I couldn’t help but tell him that if he were that good, he would have found a way to the NBA. Guess we’ll never know…
I remember us walking home, and him stopping, holding me in a semi hug, asking me “where I felt like we stood at that point”. I remember feeling completely mind fucked, saying something along the lines of “Well, I think I need to process all of this.”. He didn’t seem satisfied with that answer, but we ended the night and said we would talk more soon. We did indeed talk more soon, but the whole illuminati thing was something that I could never really get past. Dark Falcon…what a guy.
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This next guy was one that when I met him, I thought we could really be something. Declan and I met on a dating app. I remember walking into the rooftop bar where we had our first date, and when our eyes met, I felt that “oh damn” moment you feel when you meet someone and they instantly take your breath away. I’ve been on my fair share of dates where guys present themselves one way on their dating profile, and then the person you meet seems completely different. On this occasion however, I thought he was better looking in person. Beyond that, he was just so sweet and genuine and I remember the almost instant chemistry I felt when we got to talking. He was living in Los Angeles at the time, but home in Napa visiting his family. It was one of those dates where time seemed to stand still, yet it flew by in an instant. And nothing else mattered then the two of us and the conversation we were having. Before I knew it, we were both sitting on my apartment floor, next to my bookshelf. We spent a big portion of the date going back and forth talking about our favorite books, and I was showing him some of my favorites. Dorky, yes. But it was one of the things that we connected over. I remember our eyes locking at one moment, and him saying something along the lines of “Wow, this is incredible. I didn’t expect my night to go this way.” There are sometimes those borderline magical moments when you’re with someone, and you can just tell that you’re both completely on the same wavelength. And you know that the feelings of admiration were mutual. That night was one of those that I will always remember.
He spent the night that night. I remember the next morning, waking up and telling myself that I can’t let myself get excited about this guy. The phrases ringing through my head on repeat were: “there is a slim chance this will turn into anything because of the distance”, “just appreciate the night for what it was”, and “don’t fall for him”. But of course, because of the ways of the universe, he then told me how much he liked me and, despite the distance, how he would want to try to make it work with us. And of course, because I’m a hopeless romantic and just a glutton for punishment, I melted and told him how much I liked him and how I wanted to try to make it work too. Urgh.
What ensued was a fun summer where we talked all the time and I visited him a couple times in Los Angeles. I thought he was super sweet, hot as hell, and really fun. By the end of the summer, the distance and our different lives started to get in the way, and it just fell apart. I tried to see him that fall one time when I was driving home to San Diego from Napa. I told him that I was doing the drive and that it would be great to see him, and he seemed excited about it too. But then as I was driving and getting closer to LA, I would shoot him a text and tell him my ETA. And it was radio silence from him. No joke, I was literally passing his exit and I still hadn’t heard from him. I was crushed. Being stood up sucks, and that one was brutal. I had this hope that maybe we could reignite what we had, but then that experience put the kabosh on that hope. He texted me the next day saying sorry and that he fell asleep. No joke. I was driving almost 400 miles to see him, and that fucker couldn’t stay awake. I was so pissed that I didn’t respond to that text. If he couldn’t fathom how hurtful it is to stand someone up that drove hundreds of miles to see you, then there wasn’t a chance in hell that I would dignify his lame text with a response.
We were in different places, and as much as I hoped that we could rekindle something then, it just wasn’t meant to be. We didn’t talk for over 2 years after that.
We ended up reconnecting in Napa, and went on a couple dates. I was reminded of all of the reasons I liked him. He’s smart, funny, driven and just a nice guy. I think he sensed how much I liked him, and once again pulled back. He told me that he wanted to take things slow and didn’t want to hurt me again. He was in town for a few weeks and we enjoyed the time together before he was on his way again. I was definitely sad when he left but I realized that it wasn’t meant to be. It was a much needed reminder for me to be careful with my feelings and how much energy I give to people that may not reciprocate that same amount of energy back to me. I’m a bit of a hopeless romantic and thought that time had brought us back together again for a reason, and that maybe this time was the time it would work for us. But that just wasn’t the case. I’m learning how true it is that timing is everything. I’ve heard it time and time again, but am now realizing its importance. I think if circumstances were different, that this could have really been something special, but it just wasn’t in the cards for us.
I have to say though - there was a major silver lining to us reconnecting. One night I was out with him and I met a friend of his, who I then started hanging out with and we became friends. He then introduced me to an amazing group of guys who are now some of my best friends. I shared a bit more about them in column 3. Anyway, it's funny how the universe works, but all in all Oprah said it best when she said, “No experience is ever wasted. Everything has meaning.”I’ll leave it at that for this little chapter.
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The next 2 guys fall into a similar category and have left me more sad & devastated than most of the others mentioned here. And the irony is that they never even were relationships. Throughout my 20’s I have allowed myself to catch feelings for 2 men that ended up being straight. How this happened, I am still trying to figure out, but here it goes.
The first, Ben, was a guy I met through a job I once had. It was during a difficult time in my life, but this guy was one of the “bright lights” that could make my day better when he came around. He’d walk past my desk, and we’d casually drum up a conversation about pretty much anything under the sun. We’d chat for a few minutes and then each of us would go back to work. We’d take walks over to a local coffee shop whenever we could spare a few minutes in each of our days. He was one of the kindest guys I’ve ever met. Just profoundly genuine, caring and one of those guys that when you talked to them, they’d give you their full attention. I’d just fall into his eyes. They were hazel, and they were amazing. He wasn’t a “slap your hand on your knee hilarious” type, but he had his little “isms” that would, without failure, always make me laugh. He was SO good looking, but acted as if he almost didn’t even know or care, which of course, made him all that much more attractive. He simply just made my life better by being around him.
I spent years as his friend. I wouldn’t ever exaggerate the friendship to say that we were “the best of friends”, but a good friend of mine recently told me that he thinks that people come into your life either for a reason, a season or lifelong. This one was both reason and season, but unfortunately not lifelong. And it's my fault. We’ve fallen out of touch, and this is why…
After years of being his friend, I had built up this idea in my head that we might be something more than that. There were so many little things about him and our relationship that made me think that he might like me as more than a friend. I had this idea of what I thought we could be, and I let it get the better of me. I finally told him that I had feelings for him, and it turned out that he did not feel the same way, and reassured me that he was straight. He handled it in the best way possible, both with kindness and empathy. But for me, that made it even worse. I was filled with so much shame for letting myself think that it could have been anything more than what it actually was. I wouldn’t go as far to say that I was devastated, but it took me down in a way that I hadn’t experienced before. I felt crazy and stupid that I had this narrative in my head of what it could have been. I felt hurt that he didn’t feel the way I felt. Because of the shame part, with him knowing how I had truly felt about him, it was hard for me to continue a relationship with him. Whether or not he felt awkward about it, I can’t say. Like I said, he couldn’t have handled it better, but for me, it was too hard to face him. So I let the relationship fizzle out. I still feel like I fucked up something good and feel sad that I let the friendship fall apart. I miss having him as a friend.
For some reason unbeknownst to me, I let that same thing happen again a few years later. I had this other friend that I knew once, Brad. For the most part we’d always hang out one on one. He’d come over to my house and I’d cook us dinner, and vice versa. We’d geek out over wine, and enjoyed the process of learning together. We’d go for hikes and chat for hours about all sorts of things. It was funny because we rarely found ourselves in groups of other people. It was always just the two of us hanging out. There were things he’d tell me about his relationships with other women that didn’t add up to me, and made me think that he might be gay or bi. I used to think all the time that maybe he was subtly giving me hints to think that. On top of all of that, there was always just this lingering gaze between us. If you’ve ever liked someone, or felt a connection, you know this gaze. You and them just keep eye contact for a little bit longer than you normally would with anyone else. I know it sounds corny, but the gaze was just there.
One late summer day, we found ourselves at a music festival. We had been drinking for most of the day, and had the funnest day laughing, joking around, drinking and enjoying the music. At one point I mentioned to him that he was welcome to crash at my apartment that night. Somehow we got on the topic of whether he would sleep in my bed or on the couch. With a smirk on his face, he then posed the question, “You’re not going to try to hook up with me, are you?”. I was shocked he asked the question that bluntly, and the way he said it made me wonder if he was in some indirect way trying to tell me that was what he wanted. Who knows. I think I just laughed and never really answered the question. It caught me so off guard, but on the other side of the coin made me wonder if after all this time, something was finally going to happen between us. To this day, I still think about how none of my straight male friends have ever said something like that to me. In and of itself, the question could be viewed as relatively harmless, but with the context & uniqueness of our relationship in mind, it was super confusing and strange.
Later that night we were watching one of the performers and he said his back hurt, so we went over to some seats at the side of the crowd, and watched the concert from there. We sat next to each other for an hour or so, during which we had both moved closer to each other. It was loud so we found ourselves talking into each other's ears. Before the show was over, he asked if I wanted to “get out of here”, and I said yes. We went back to my apartment, and sat on my couch. I don’t remember exactly what we were talking about, but at one point there was this silence, and I found myself drifting away thinking about him. I looked down at the floor, wondering if this was finally when one of us was going to make a move. It was one of those moments that was so tense, you could cut that tension with a knife. He looked over at me and said, “Hey you, what's going on in that head of yours?” I looked back at him, took a deep breath, and said “Oh nothing…just nothing”. I couldn’t bring myself to make a move. There was another few seconds of silence that felt like a year. I swear you could cut the tension in the room with a knife. After a few moments, he abruptly said that he was going to go home. I told him that he should just spend the night, and that he could just sleep on my couch. Since we had both been drinking, I really didn’t think he should have driven. Though, he was taller and could probably handle more liquor than me. But he insisted that he was fine and was set on going home.
The next morning I woke up hungover and confused. I replayed the night and the past year in my head over and over, and none of it added up. I decided that I didn’t want to live in this “relationship purgatory” anymore, and decided I was going to tell him how I felt. I was still scarred from the guy mentioned above, and didn’t have the courage to tell him to his face, so I wrote a text. I spelled out my feelings, saying “maybe I was imagining it and I’m just a lunatic, but I felt like there was a connection with us that was more than friends”. He replied with a very kind worded text, similar to the last response I’d received from Ben, and I felt like I was having deja vu. I couldn’t believe this was happening to me again. How did I get here? Am I so thirsty for a relationship that I’m imagining one when it doesn’t exist? There were so many moments and interactions in our friendship that made me think that there was something more there. I was crushed, and so ashamed. Like I said, he couldn't have handled it better, saying that he hoped this didn’t change our friendship. But in my mind, I couldn’t let myself face him again. It was just too much. I was a bit of a wreck, and my self esteem was at an all time low. Similar to before with Ben, I was in a shame spiral. I was hurt, embarrassed, confused and angry with myself.
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Now this next one REALLY messed me up. I met this next guy at an event of sorts in Napa, and there was just this something about him that drew me to him. Vic was a bit on the rugged side, and there was this way about him that told me he was a “good guy”. He’s a winemaker and I liked that about him. And there was no doubt there was chemistry between us. We went on a series of dates over the course of about 6 months and each one was pretty great. We had a connection and it just felt comfortable. It was easy being with him. The way he described what he wanted his life to look like matched very closely to what I saw for mine. I think I fell in love with the idea of what we could have been together, but not really with him. Somehow our lives never quite fit together. He had a relationship that had just recently ended, and was still dealing with that. I felt like we were two sides of a sweatshirt with a zipper that would always snag on the fabric, and never move all that far up.
I would tell my friends at the time that he was just like Mr. Big, because he would pop in and out of my life (Sex and the City reference…IYKYK. Don’t even get me started about how Carrie should have ended up with Aidan). Anyway, right about when I would almost forget about him and move on, he would show up and I’d fall for him over and over again. He would tell me how much he liked me, talk about how he could see a future with us and what a good match he thought we were, but then he’d fall off the radar for months. Only to come back again and repeat the cycle. It was with him that I felt like I really finally understood how the laws of attraction work. Because the farther away we would get from each other, the more he would want me. I’d run into him at my favorite dive bar, for example, and at the beginning of our conversation want nothing to do with him, but by the end, we’d be drunkenly making out. Sound familiar? ;)
Anyway, he’s out of the picture (for now, hopefully for good), and I think that chapter has finally closed.
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When it comes to dating, I feel like I'm a work in progress. Day by day, I'm slowly just figuring it out by trial and error. I can’t say that at 30 I’ve ever truly been in love, romantically that is. I think I’ve grown strong feelings for someone, and cared about them, but I can’t say I’ve truly fallen in love with anyone.
I can’t say that I fall for guys too often, but when I do, I often fall hard. The thing is that when I do find someone that I’m interested in, my mind can’t help but look down the road to imagine what life could be like if we were together. Key word “could” be, not what it currently is. What I’m learning now is how to just enjoy where I am in a relationship, to be at peace with where it's at, and let it unfold organically. I’ve spent so much energy trying to make things something that they weren’t, and I think there is something to be said for letting it just take its course. To not force things that aren’t meant to be, and to let what is meant to be happen when the time is right. I’ve been told that the quickest way to speed up is to slow down. So that's what I’ve been doing lately. And I think the more I just relax, be myself and have fun, the more likely I am to attract the right person.
I’ve learned to be careful with who I give energy to. My friends (many of which moonlight as excellent dating coaches) tell me that I have so much to offer someone, but that I need to learn the give and take of dating more, and not invest in someone when they haven’t shown me that they will invest in me too. A little nugget that one of my favorite dating coaches has told me, is that more desire equals less power. While I don’t like “playing games” at all in dating, I have learned that it's important to at least know the game. And its key to know that its human nature to want what is scarce and unavailable. The point I’m trying to make is that overextending too early can often be found unattractive. I can’t believe it took me 30 years to learn that, but here we are. I’ve spent so much time giving and giving, when all the while it was probably making them like me less, not more. I’m not saying to not be giving and generous with your partner. I’m just saying I’ve learned I shouldn’t be giving and generous when they haven’t proved that they will do the same for me.
I love the quote, “When someone shows you who they are, believe them.” And I need to remind myself of it often. Too often have I had to learn the same lesson from someone more than once, and let someone back into my life when they have already shown me that they probably shouldn't be there in the first place. That being said, I’ve learned something from all of these situations. Too often have I made excuses, rationalized and told myself that “things would be different this time around”. Too often have I gotten to a place of being centered, and happy with where I am in life, and then let myself get pulled sideways by someone. I become so consumed by the idea of being with them, that I forget about all of the other positive things in my life. And then I’m left feeling disappointed when it doesn’t work out. I will work so hard to “fill my cup” and do the work on myself, but then I pour so much into someone else's. Theirs is left full - so full in fact, that they don’t want any more of me. And by the end of it, my cup is left empty.
I think the process of growing up in the closet can cause a struggle with not knowing and fully realizing your self worth. After all, how could you when the world is telling you that you aren’t good enough? And as a result we settle for less than we deserve, because we haven’t fully identified and grown confident enough with who we are and what we deserve. I’ve spent so much time banging my head against the wall, wondering why I haven’t found love yet. I often suspect that it's partly because I’ve spent too much time trying to make things work with guys that don’t treat me how I deserve to be treated. On one hand, I think they are so great and total catches, but then on the other hand I ask myself, “how much have they poured into my cup?”, and more often than not, it's not very much. And a big part of the reason they haven’t is because I haven’t asked them to because I’m not confident enough to so. And sadly, that's because sometimes I don’t think its worth it…that I’m worth it, to make the ask.
Bottom line - we accept the love we think we deserve. And I think it's when we realize our self worth that we can then draw the line in the sand. When we can confidently & clearly communicate what we want, need and won’t settle for. That's when I suspect the right person comes along.
For now, I’m just trying my best to do the work on myself, fill my cup, know my worth and then just “let it be”.
