Date #35 & #36: From High Hopes to Hard Passes

February 17, 2024

I met #35 at Punch Bowl Social in Arlington, VA. By this time I’m already familiar with the place so although I like trying new places, I was glad to be going somewhere I’ve been a few times before and have always had a good time.

I don’t remember specifically from his pictures what I thought of his looks but I do remember I was pleasantly surprised when he walked up. He wasn’t necessarily my type to a T but he wasn’t ugly by my standards either. Not gonna lie… we hit it off instantly; a complete 180 from the last date, which made it better in my opinion. 

I remember the date being a lot of laughs. I felt comfortable asking him anything. We first met up at the top level that is more lively with bowling and games and the bar. We got a drink or two then decided to go to the second level with less of a crowd to enjoy some food and a quieter setting.

When we headed down it was better for more conversation and we shared a bowl of loaded fries. More laughs and conversation that lasted ‘til the place closed. The few things that did attract me was that he was established in his career but also has further goals for himself, we wanted the same thing long-term (on the fence with marriage, didn’t want kids), he complimented me saying I was really pretty, and above all he was also an Aquarius which I’ve always wanted to date one to see what that experience was like.

But there were also a few things I was wary of. For one this date was in February and he said his last breakup was in December. It was still fresh in my mind where I had to secretly question if this was a rebound sort of thing. Another thing that made me hesitate was when I was asking what his hobbies were and he said “partying”. I’m not one to knock someone’s hobby butttt idkkk for that to be a hobby of his was just a bit of a turn off for me.

One of the new rules I had now that I was in my “relationship era” was that I didn’t want to give my number out until after the first date. No reason for my number to be in a randos phone if I had no plans of seeing him again. I explained this to each guy on Hinge when they did ask for my number and most did understand. Those who didn’t obviously wasn’t seeing me.

So anywho #34 walked me to my car which is when he asked me on a second date and I explained in another post that I don’t like guys asking for a second date in person but I really did want to see him again, so I didn’t mind and I even agreed. At this point is when he also asked for my number. It was a good date and I was excited for the second which happened the very next morning when we went for brunch.

February 18, 2024

We went to Silver Diner in Lanham, MD, not far from me. He chose it knowing specifically that it was closer to me than to him. We must’ve gone at a busy time because there was a good wait time, long enough to where we decided to just wait in his car as opposed to inside. I thought it would’ve been maybe awkward but conversation was still as funny and comfortable as the night before, but unfortunately it died down sometime during brunch.

Now… there was another thing that gave me pause about him. Again, I wasn’t talking to my friends about who I was dating so I really was trying to work through it myself until I really did have to consult one friend (and my therapist) about it.

Let’s rewind to the beginning of the first date. At the bar on the top floor, as we were enjoying our drinks, there was a lady sitting next to us with another drink. I told him that it looked good which he then tapped her and asked her what the drink was. But when he was pointing to the drink… he did it in a way that seemed a bit feminine to me. Now I’m not one to write off one action so at the time I really did push it out of my head. Until at another time we were talking and he stuck his tongue out the way Megan the Stallion be doing a lot – not just once but a good two or three times, in a way you wouldn’t expect a man to really do. Along with that I felt like his voice possibly had a bit of a twang to it. Lastly, he kept sayin ‘chiiiile’, not only saying the word, but dragging it out too. I personally don’t know many straight guys who use this word but I know alot of gay guys who uses it. So all of these put together had me questioning a few things.

With these four attributes, I suspected he may have been gay. I even had a gay friend of mine look at his pictures and listen to voice notes to see if he picked up on anything which he stated there may be a possibility but he couldn’t call it forsure. When he asked how his upkeep was I told him he does smell good and his nails were impressively clean so he said he may have been metrosexual. I then told him that he was a mechanic or one of those fix-it type of jobs and he said "well that doesn't make sense". Lol it was a mystery to all of us.

Now I’ll be honest with yall… I truly have no problems dating a bisexual guy I mean I’ve dated one before. However, being downlow is understandably one of women’s fears when dating men and I didn’t know how to bring this up… especially without him being offended. But my therapist talked me into asking because if I am going to be dating him I do have the right to know. Luckily, we did get into a conversation about sexuality and I ended up asking him which he assured me he was straight so there wasn’t much I could do but take his word on it. And he also wasn’t offended by me asking. But my suspicions of him being gay or at least downlow wasn’t the only off putting thing about him.

Fast forward to the end of the first date when he walked me to my car, he jokingly invited himself over to my place. One thing I also didn’t want to do while dating around was to inform guys that I had my own place… obviously for safety reasons. But during our date it came out and I kicked myself over it ever since. The first time he invited himself over I let it slide… until he mentioned it a good three more times.

During brunch the next day he had told me he was going to go to his sister’s house since she lived close because he was going to DC later that night and didn’t want to drive all the way back home. Periodically throughout the date he would mention going over there then end with “...since someone doesn’t want me to go to their place”, and sir why would I? I decided that I would bring up how uncomfortable this made me but of course wanted a good time to do it. That night, since he was going to his sister's place, and then going out with his friends, I thought that day/night wouldn’t be the best time. We parted ways, went to our respective destinations, continued to talk… until he mentioned coming to my place again, before I even had a chance to tell him that this bothered me. Like I’m not agreeing to you coming to my house, how many times do I have to give you an awkward response before you let it go?! I instantly ended it right then and there. But it was one of those weird conversations where he tried to explain that he was kidding and “you’re still a stranger why would I want to go over there?” as if any man wouldn’t jump at the opportunity of going to a woman’s house if given the chance… especially after a thousand times of “joking” about it. And I explained my side and I knew he was going to hang with his friends that night so the conversation kind of just ended in the middle. He texted me the next morning as if I didn’t end things between us but I had to make it clear that I was no longer interested in dating him.

But I will be honest, I thought it over. I remembered how my friend said I cut guys off for the smallest things and don’t give guys a chance to fuck up. Although it was obvious that he kept trying to come back to my place, I decided after a few days or so to hit him up. I told him that I probably did react abruptly, I didn’t fully express my side of things and how uncomfortable I was with this joke, and that it wasn’t fair to him to not explain his side of things either. I told him I was open to dating again if he was and he agreed.

March 1, 2024

Our dating period didn’t last much longer after this. Matter fact we only had one more date after that conversation before I ended things again. Since it was the third date and I typically take guys out on the third date, I had planned for us to go to Spices Asian Restaurant and Sushi Bar in NW DC. It was a decent time but I think at this point I was just trying to force something that kind of already died. After dinner we walked down the block to Atomic Billiards which was on my list of places to go buuuut it wasn’t exactly our scene. Very much preppy white college student vibes. And they said it was going to be about an hour and a half to two hours wait for a pool table. We sat there for a little bit looking up other pool halls because I really did want to play pool and I also felt bad that part of my plan fell through. We decided to go with old faithful though – Dave & Busters near my place. It was the weekend, already late, so no surprises there was a wait for a pool table there too. We just sat at the bar enjoying a drink and the vibes just didn’t hit like the first date. I knew this was going to be the last one.

We left once D&B closed and yall know I love me a lil parked car conversation but I wasn’t even in the mood which tells you how over the date I was. We weren’t on the same page clearly because he decided to ask for a kiss and… despite my better judgement, I did kiss him. But I wasn’t about to stay for a whole makeout session so I left and shortly after that I ended things with him again. This was rushed by the fact he invited me over for a “movie night” at his place that night and it didn’t even sound remotely intriguing. I could tell he wasn’t happy with this decision as his responses were cold, even months later when I texted him and past dates to ask for a word or sentence to describe our date(s) and he responded with “it wasn’t bad.” Wasn’t the worst response I got that day.

February 22, 2024

Date #35 was hands down the best conversation I’ve ever had on a date. That was one thing that stood out about this one. I arrived at Kung Fu Tea in College Park, MD (fun fact I drove down that same street recently as I was leaving some other place and realized I had 9 other dates on that exact street despite me not being too fond of the area… I think it just reminds me of a small college town).

But anywho… so I arrived and I saw him through the window looking down at his phone and I smiled so hard because off guard he was really cute. When I did approach him though and the more I got to know him I’d describe him moreso as adorable than cute. He was this short and skinny filipino-spaniard guy. My first time ever being on a date with one, so I was already intrigued on what his background was like.

It was an awkward introduction though because when I walked up I just kind of stood there while he stayed seated as we talked a bit. Then I was like “what are you going to order?” and he said “oh I already ordered” which I thought was a bit off so I joked about how he didn’t wait for me and he looked so embarrassed and started stuttering and was like “oh order anything you want I can pay for it!” and then I started stuttering myself because I was really kidding but him being embarrassed kind of caught me off guard. Just that glitchy reaction already kind of put me on edge. Along with this I also noticed he was dressed down in a sports jacket and shorts which I later found out he came straight from coaching so I'm like… ok, not even gonna get semi-dressed or freshen up or anything. Had me looking a little overdressed since I was wearing a sweater, jeans, and boots.

So of course he got his drink first and then I ordered and as we were waiting for mine we sat at a table with awkward minimal talk until we grew more comfortable and moved to a corner table. It wasn’t a crowded place to begin with so for most of the date we were the only ones in there which made the conversation seem more intimate and personal… and when I say personal I mean just that. I’ll be the first to admit that I zone out when someone is talking too long but I was latching onto every single word this man was telling me because I was so interested in his life story. So interesting to the point where the second I got home I literally typed out every detail that I remembered from the date (which is big because I’m very forgetful, especially after you only tell me something once or I meet you only one time). It was 3 pages worth of information but I’m not going to share most of it because although y'all don’t know who this man is, the information feels like an overshare on my part.

There were two things that stood out on the date to me though. One being that he was adopted by a (white man, Filipina woman) catholic conservative family who does not approve of him dating outside of his race and they had explicitly stated that they would not be attending his wedding if the girl wasn’t catholic. Although he was fine with that, he knows it would be a hard conversation to have with his family and future spouse when it comes down to it… especially since he hasn’t even dated any asian girls, a few spanish women, and three black girls “which were the best moments of his life”. Boy am I praying for his future wife.

Another thing that stood out was a comment he made. We’re in the same career field and a bit of an insecurity on my part – he has made it much farther than me career wise despite being a couple years younger than me. He had admitted that he has used his white privilege via his dad to get through school and to get jobs. I won’t lie, this is definitely something that I might become resentful of in the future being a black woman already having to struggle to get half as far as everyone else, while dating someone who at least acknowledges that he uses his privilege, all while his white father wouldn’t even approve of us dating. Life is already hard and these weren't problems I wanted added to my life.

Other interesting facts about him was that he coaches tennis, plays the piano and the guitar, knows Spanish, and is a photographer. Now as someone who attempted and sucked at tennis, always wanted to learn how to play the piano, and took 4 Spanish classes and still doesn’t know a lick of it… I was impressed. Especially too because the guy I was dating at the same time as him whose hobby was “partying”, this one seemed to have a lot more going for himself.

One off putting quality about him while on the date though was his constant sexual jokes and innuendos. However, he did give me a whole TedTalk about his intentions (which he brought up himself) stating that although he does joke about sex alot, that it isn’t the only thing he’s after. He admitted wanting to wait because it is sacred to him and he wants to share his energy with someone special because as soon as they do it he’ll always be a part of that person, so wants to make sure it is the right timing for the two. He opened up very quickly which may or may not have been a red flag. 

After running down his whole life story he asked about me and I honestly felt a bit inadequate I hate to say. I didn’t feel as interesting as he was, and my life stories couldn’t measure up to his. But he forsure studied me, maybe a little too much. He told me more about myself than I could tell him. He told me every single thing that was in my Hinge bio and on my IG  – the specific prompts on my bio, he asked about my tattoos, he knew I liked to travel, he knew I didn’t want kids, he mentioned the age difference, he could tell I loved movies, he knows I like to drink (not a problem for him although he doesn’t drink himself), he remembers what type of work I do (even though we’re both in the mental health field), he remembers I know Sign Language, he mentioned me wanting a long-term relationship…

Although his life moments have been the most interesting of any guy I’ve been on a date with, I hate to say that physically, not looks wise, but body wise, I was a little turned off. Not only was he short but he was also skinny. I’m sure I weigh more than him and I didn’t know if I wanted to date someone I weighed more than. It doesn’t give that “protective” feeling I crave in a partner.

After the smoothies, we ordered some wings and ate in his car although I couldn’t truly enjoy it because for one we were in a Tesla and for two he said he doesn’t eat in his car because he’s a neat freak (samesies) but didn’t want to invite me up so that I’m more comfortable (which was refreshing to hear based on what I went through with the last guy). It was getting late and he said he didn't want to be disrespectful and wanted to go to bed at a decent hour – it was 11pm. I honestly found myself a bit sad that the night had come to an end.

I had either never been this interested in a guy or I had never been on a date with anyone that interesting because the fact that I was able to not only remember but type out the whole date was impressive. I typed, “even if this does not have a romantic ending I can only pray that we at least be good friends. We also talked about if he is no longer interested in a romantic sense how would he end things with me he said he would ask if I would want to shift to another level of friendship which I can only respect on a surface level as I of course don't know if he will follow through with this”.

February 27, 2024

Our second date – don’t judge me – was to Denny’s lol (I don’t need to provide a link for that right?). But I was really craving their apple crisp one day, and he told me to pick the next spot we go to. I thought it only made sense right? And he was down. I ate before because I knew I was just going to get the dessert, and dressed down a bit. While he on the other hand dressed up more than the first date, and ordered steak. Our little outing was nice, until we then went to his car and I think that’s where things took a turn for me. He asked if he could kiss me, and I agreed but… the kiss was not it. He wasn’t bad, it just– I didn’t get that excited feeling I get when I’m really into someone. Let alone he had small lips so it already was kind of weird for me.

But as we’re in the car I had mentioned how I like nice walks and we got out and walked up and down the block just talking, holding hands, occasional kisses here and there. I knew then it wasn’t going to last much longer with him. It started to rain so we thought it best to end the date there.

February 29, 2024

I unexpectedly saw him two days later. I was telling him about this Eric Bellinger concert I was going to but was upset that I felt myself catching a cold. But I already paid for those tickets and Eric was a fav at some point in time so I wasn’t missing this concert. I had debated if I would Uber or drive to which #36 said he wasn’t far from the venue. He told me I could drive to his place, leave my car in a church parking lot near his place while he takes me to the concert, and he’ll pick me up after. I thought this was really sweet, so I took him up on his offer.

When I did arrive he had given me this care package with medicines, teas, vix, cough-drops… I’m talkin the whole medicine cabinet. He even included a box of hot chocolate because he remembered I liked it. Although it may seem small to some, it truly was one of the most thoughtful gestures a guy has given me. And to this day I still think about that everytime I’m sick because I actually kept the bag he gave me and I keep all my medicine in there now.

But anywho so yes I was nervous to leave my car in some random parking lot but he assured me it was safe, the concert was really fun, and then he picked me up as he stated he would. Didn’t need to wait long for an uber or fight concert traffic or anything.

When he dropped me off at my car I absentmindedly mentioned I needed gas but because it was late I would do it in the morning. He said he would follow me to the gas station and pay for my gas as well. I felt bad knowing I wasn’t going to keep him around long so I tried to decline but he said it would make him feel better knowing I made it home safely (I mean I had enough to get home but…) I wasn’t going to fight this man who wanted to pay for my gas. So we arrived and we literally sat there at the whole pump just talking. I probably would’ve said let’s drive somewhere else but there was barely any cars out that late, no one was waiting for the pump.

A few days after that he saw my date on IG with the other guy I was dating (#35). He commented on one of my boomerang stories asking if I was twerking and I’m like… that’s a weird question. I don’t think I would’ve classified it as me twerking, I was really just doing a silly dance in the rain with my umbrella. We got into a lengthy conversation about… really I don’t even remember. Something about him being insecure about girls always choosing someone taller, more good looking, etc., and how he was uncomfortable with me choosing another guy over him and I’m like ? I didn’t even choose. I only saw the both of yall 3 times… but because I knew I was going to end it I didn’t even argue with him and told him that I agreed on us going our separate ways. And then he asked me why and I’m like omg why does that matter at this point if you wanted it to end too… but I told him it was all the sex jokes he couldn’t stop making and the sexual innuendos he couldn’t stop forcing into every sentence. He started going on and on again about his insecurity and I just– understood but also not an excuse. I can’t recall the full conversation because he ended up calling me but these were the main points I remembered. I wanted someone who was confident and he just wasn’t that. Very sweet but seems to be someone who could be a pushover and that wasn’t someone I wanted to be with.

He said we could be friends and I was fine with that but then days later I noticed he unfollowed me which was weird because why even bring up the friend thing? Months later when I hit him up for his word/sentence about our dates he said “Hello. Thanks for letting me know. I’m not feeling it. Take Care!” 

Although he was getting help for it, he did have a lot of mental health issues and insecurity he was trying to work through, along with family issues that I don’t think I could have dealt with. I’m glad he told me from the jump but realistically it probably wasn’t something I could handle in the long run so it’s better that it ended when it did. I still wish him nothing but the best.