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Writer's pictureRaven James

Adventures in (Awkward) Dating


Dating can be confusing. And as someone with a more analytical personality, I'm not into that.


Not too long ago, a friend of mine posted on her Instagram story her frustration with dating in the DMV area. She received many responses reiterating the same idea:


Dating in this area is so difficult

Everyone's so obsessed with being 'a savage'

No one's ready to settle down until they're, like, 40!


Scrolling through these responses, I couldn't help but think...where have I heard this before? It turns out this narrative was so familiar because I had just heard some other group of friends (all either from the west coast or the midwest) expressing the same frustrations just a few weeks ago. Clearly, this isn't just something exclusive to my area.

It started making me think back on my own dating experience while living in this area and, sure enough, the experiences were less than ideal. Not so much because of them not budding into relationships, but because of the overall dynamic. It always felt like something wasn't quite right with our interactions. For me, dating wasn't just frustrating...it was downright confusing.


But the more I've looked into it, the more it becomes apparent that this isn't a 'regional' thing. As much as I would like to not make this into a 'millennial' thing, it looks like it is (once again) a millennial thing.

For now, I only want to speak on my experience and perspective as well as highlight some of the helpful things I've taken away from people in my life who are in successful/healthy relationships. But let's get one thing straight:


I don't know what I'm doing.


Or at least that's how it felt for a very long time. I have the self-image to admit that I had no clue what I was doing when it came to dating. I was clueless and awkward. And as much as I would love to be that charming type of awkward, you know the kind that's cute and endearing? Unfortunately, that's not my reality. I do things and people want to know what is wrong with me. But it's all good, I'm charming in my own right. With that being said, my experience in dating as an adult has been quite minimal; my last "serious" relationship ended the second semester of my Freshman year of college (so about 7 years ago). Between then and now, I've dated here and there and all of these experiences have been very....educational.


My parents are pretty traditional, and a lot of that has rubbed off on me and my own expectations. I didn't receive that much dating advice from my mom (bear in mind she's been married to my dad since she was 20), but one thing she indirectly emphasized was the idea of being pursued. In other words, she didn't like the idea of me chasing after a guy. Rather, a guy should show his respect towards me by courting and actively pursuing me. She didn't like the idea of me driving over to a boyfriend's house, nor did she like the idea of me rushing outside in response to an "I'm here" text when he could've just come to the door to greet me. The same goes for opening doors, pulling out chairs, making sure I'm not walking on the side of traffic on the sidewalk, etc. Because of this, I just thought all of that was the norm for everyone.

So you can imagine my surprise when a guy I was seeing hit me with the "I'm outside" text for the first time. I was kind of puzzled. Not really knowing how to respond, I took another minute to get ready and came out. After I got into his car I kind of joked about it in an attempt to laugh it off. But what threw me off wasn't necessarily the fact that he didn't want to come to meet me at the door, it was how incredibly adamant he was about not doing it. It was that very small, seemingly insignificant thing that started making me question myself:


Is it weird that I want him to come to the door?....Am I being unrealistic? Is that considered high-maintenance? Are my ideas on courtship considered outdated? Why does this bother me so much? Maybe it's not as big of a deal as I thought....


I'm not expecting you as the reader to relate to these feelings, I do understand that I have a way of overanalyzing most of my social encounters (it comes with being an Awkward Penguin).

This article from Rolling Stone offers a perspective that I can relate to heavily. Essentially, people in my age range (aka millennials) may have some difficulty with dating because we're essentially caught between two worlds. We grew up in a time in which social media technologies were being introduced, but not necessarily required for social/romantic relationships. But our current era thrives on social interactions with the assistance of social media and dating apps. In other words, a part of us would like to have that traditional sense of dating in which we meet someone organically, get to know them, and take things slow. But then there's another part of us that is caught up in the way things are now: dating apps, social media, text conversations, etc, and keeping up with those norms. We also can't deny the convenience of these tools, especially if you're dealing more with a fast-paced lifestyle living in a metropolitan area.

Throughout the times I have dated, even if I did become comfortable with that person, there was still something off: I never knew the "proper way" to conduct myself. I felt the need to be so hyper-conscious of all my actions to avoid being misunderstood: What if he thinks I'm rushing things? Is it clingy if I do this? Am I being standoffish? Am I sharing too little? Am I sharing too much? Personally, I don't think this is the right way to date. I shouldn't have to be second-guessing myself and playing mental ping-pong about all of my interactions with this person.

So we've established that I typically don't know what I'm doing. But luckily for me, I've put myself around people who actually do. Thanks to those positive influences in my life, some reading, (and some try-fail-adjust), here are some things that I've learned when it comes to dating.


1) Know What You Want Beforehand

Millennials get a pretty bad rep when it comes to the idea of commitment. And there's some truth to that. We have a tendency to ask ourselves: "What if I'm missing out on something better?" We can't even commit to making plans most of the time because we want to make sure nothing more fun is happening that day our friend invites us out. I find the same goes for dating. However, we can resolve a lot of the guesswork and 'what ifs' if we just take the time to identify what it is we actually want.

A year or two ago, one of my good friends and I were talking about dating, relationships, etc. She herself has been happily married to her husband for over 10 years, so it's safe to say she has some credibility. Marriage was definitely not (and lowkey still isn't) my main priority, but she convinced me that it would be a good idea to create a list of qualities that I want in my future husband. I was hesitant at first but ended up giving it a shot. To my surprise, when I would go out on dates I actually had something to go off of when it came to how I felt about that person and if I really saw it going anywhere.

This list isn't really a checklist, so much as a number of qualities that you find important in the person you want to commit to. Making that list made me ask myself some questions: What are my non-negotiables? What are qualities that he absolutely must have? What are qualities that would be nice, but not mandatory? What are some things that are absolute deal breakers? When we know what we want, our vision is clearer and we're able to set the right boundaries for ourselves and our suitors. And we're a lot less likely to have the 'what-ifs' rearing in the back of our minds. One thing to take into account, however, is we shouldn't expect 'the perfect person'. If you make a list of 10 qualities, for example, that person is probably gonna meet 8 of them at the most. That's why it's important to really hash out those non-negotiables.


2) Be Clear about Your Intentions

This goes back to the idea of knowing what you want. If you or the other person won't know what you want to get out of this courtship, it can easily roll into becoming a "situationship" as the kids call it.

I'll admit it can be awkward, but for me, it's very important to know the other person's intentions before getting in too deep. I know from experience that finding out too late is a very not fun thing. Along with intentions, maybe some other things your person of interest should know before they become emotionally vested in you; maybe you have career plans that will cause you to have to move out of the area, or maybe you have some huge financial responsibilities that affect your lifestyle, or you're not sexually active. Share what you're comfortable with sharing, but if it's something that could impact the person who is considering a serious relationship with you, it's best to lean on the side of transparency.

Knowing each other's intentions can be a real time saver, and it can also save you from some hurt feelings. I was seeing a guy for about 2 or 3 months before he came to the conclusion that he did not want to pursue me seriously. While the "intentions" conversation didn't actually happen, I could already see that he was displaying qualities and behaviors that were questionable. While it was hurtful at first (as rejection can be), it was pretty easy to get over because through his actions he unintentionally made his intentions clear before we got to that point whether he knew it or not. A word of wisdom I picked up from my mentor, though it was in the context of business negotiation I feel like it's applicable here too:

Never sit down at a table with someone that you're not willing to walk away from.

3) Don't Fall into the Comparison Game

This year, I've seen several friends announce engagements. And that's great! I'm glad that so many people are taking that big step in their relationships. But I understand that not everyone is as nonchalant as me when it comes to marriage. Because it's not a big priority for me right now, it's a lot easier for me to be genuinely happy for these friends and acquaintances. But for someone who may be more anxious about getting married and starting a family sooner than later, it can be tough seeing everyone else do that. Not to say these people aren't happy for their friends, but they may be more susceptible to comparing their lives to someone else's. I've said this before in another post, but we always have to remember that our lives are not a race. Everyone's pace is different; some people get married right after high school, others go to college and establish a career first, and some wait for several more years. Really, we can't go comparing our story to someone else's, especially if they're on page 220 and you're on page 22. Instead of focusing on everyone around you, it would be best to focus on yourself and your own development instead. This leads to the next one:


4) Continue to Grow Yourself

It's one thing to know what you want in a person, but it's important to keep asking yourself: Do I display qualities that will attract a person like that? This isn't about physical attributes, but about character. Something that my positive influences say is that we should always strive to be the person we want to attract. We have to gain a solid understanding of ourselves and be sure that we're actually prepared for that person before they step into the picture. Being secure in who you are and continuing to grow to your fullest potential should honestly be the number one priority. I'm not interested in finding 'another half', and personally I don't really believe in that. Why would anyone want to be with half of a person? And why should your fullness lie in whether or not another person is there? We can both just be whole together and make 200%, right?


As for me, I'm pretty happy being single. And while marriage isn't necessarily in the forefront of my mind right now, I still think these things are still important to bear in mind for when I do get back into the dating scene. Dating can be weird, awkward, and ambiguous, but just remember that it doesn't have to be.


-Raven


*Originally published on October 5, 2018

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