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Romantic Relationship Woes

Today, my younger sister moves in with her boyfriend, and as the eldest sibling, it truly blows my mind she’s at a point in life where she can do that. I remember crying when she broke her arm in the forth grade. I remember all those late school nights watching her softball games.

With each step she takes in her adulting journey, I think about where I am in mine, and how, though I’m an extrovert (sorta), I am still lacking in the relationship department, especially romantic relationships (yes, this is another one of those blog posts).

When I think about having a romantic relationship, I think about how picky I am. I’m pretty sure part of my pickiness stems from some hesitancies, which honestly stem from fear (fears I need to shake).

FINANCES: What if I get with someone who is put off about me being in debt (shout out to student loans, car notes, & credit cards)? I wouldn’t dare ask him for help, but what if my desire to live life over stressing about debt is a massive turn off for him? Is being in debt a relationship red flag? Even if I’m consistent with my payments and have been since the beginning of time? I’ve had a unique life of stuggle, amplified by a consistent desire for independence, and that definitely shows up in my finances.

PHYSIQUE: It kind of blows my mind teenage boys find me attractive (which disappears when they realize I’m in my early 20s). Recently, I was editing a Mother’s Day in My life, which may or may not be up when this is being written, and I realized just how bad my posture is. Like WOW. Is it from years of being scrunched in a ball to escape in a book? Is it from years of sleeping in a fetal position on twin beds I was too tall for? I’m very close to giving the Hunchback of Notre Dame a run for his money.

Let’s not even get into the wonderful gene of fast growing hair my father graced me with. I’ve talked about being a woman who grows hair everywhere at a rapid rate, but I feel like it’s getting worse. There are ruined pictures and videos because of my upper lip hair. I can start the day off with smooth pits and end the day being able to braid my under arms.

I’ve also recently learned some men get intimidated because we have the same shoe size, but if there’s one thing I’m not going to apologize for, it’s having above-average-sized feet (though I will cry about it).

EXPERIENCE: Well, lack of. I’ve been very open about still being a virgin, so I won’t go into too much detail here. Since I’m so inexperienced, what if I’m bad? What if I never get good? What if I reach the point of wanting to be adventurous (or “freaky” as the young kids eloquently put it), and he doesn’t want that? When it comes time for my first real kiss, what if I don’t respond well? What if my overactive saliva glands make themselves known and ruin everything?

PASSIONS: If there’s one thing I’m going to do, it’s respect the heck out of whatever man I end up with (whether temporarily dating or forever married and dating). With that being said, I won’t film him or write about him or share pictures of him on any platform if he doesn’t want me to. Yes, Simply Jamilah is a documentation of my life and a way to cope with life and everything that changes as I grow up. Though this man would be a part of my life, our intimacy will be as private as he wants it to be. But what if I tell him I have a blog and a podcast and he suddenly doesn’t want anything to do with me? What if he doesn’t accept this part of me? What if having these platforms and everything I said/say/will say will create a rift in our relationship? My heart broke for Meghan Markle when she had to give up the blog she loved as a regulation (not the right word, but my brain was hurting trying to find it so just roll with it) to be with the man she loves. I don’t want to do that.

INTERESTS: What if I have to suffer through nightmares caused by horror movies because I watched a horror movie to make him happy? What if he doesn’t support me or doesn’t want to play with/against me during a makeshift soccer game? I know it’s good for individuals to have their respective interests, but what if I endlessly support his, and he continuously gives me nothing in return? I want to be able to watch movies or TV shows together, cuddled up on my cheap blue couch (or his probably expensive camel-colored one) and not consistently hear his disgust in what we’re watching. I guess I just want a balance of shared and polar opposite interests.


As I wrote this, I feel like this is something I’ve talked about on the podcast before. I think I go so long without talking about my singleness that I literally decide to talk about it again (I wish I was kidding). Having a folder on my notes app dedicated to The Man of My Dreams definitely helps with this happening a lot less.

With all of this being said, I still refuse to give dating apps another try. The hopeless romantic in me thinks (more like hopes) it will happen naturally.

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