Debrief: My First Real Relationship

In Dating and Relationships by jfree0072 Comments

Wow…I can’t say, “I’ve never had a girlfriend” anymore. I was in a real relationship…it’s weird to even think about cause for almost 23 years I was technically single. It was awesome and weird and crazy all at the same time so I thought it deserved a post. This is my debrief from my first real relationship ever.

Setting the Stage

For those of you keeping track this is the same girl from the post So Are You Dating? For some more background you should definitely go and read that first.


Making Friends After College in the “Real World”

So Are You Dating?

Pros of My First Real Relationship

Nice to have someone to care about and care about you

I guess this is the real reason I wanted a relationship. It’s suuuper sappy so I’ll get through this one fast. It is a great feeling to find someone that you can care about and that also cares about you.

It is kinda hard to find!

I definitely loved the “Good Morning” texts and having someone to share good and bad news with was really great because I didn’t feel like I was going through things alone.

Ok enough of this super sappy stuff let’s continue to a different super sappy pro of being in a relationship.

It has to be this way, I’m a hopeless romantic.

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She is probably the sweetest person I’ve ever met

Wow! Some people are really nice, but damn!

She was one of the sweetest people ever maybe tied for first with another girl I dated (we’ll talk about that later). Anytime I had a problem she would be right there to try and help me feel better. She would text to make sure my day was going well and just to say hey if we hadn’t talked in a little while.

She was also really nice to other people too. It’s one thing to be nice to the person you are dating, but she cared about her friends the same way. She was so genuinely concerned about their happiness that it would make her upset if they weren’t. I love my friends, the Boys are like family, but I was shocked by how much their lives affected her.Debrief: My First Real Relationship

Who is this sweet??? (This was actually a little too sweet for me, low-key)

We got to go to some really fun places together

Dating someone usually gives you a “go to” person to hangout with. Someone that is always down to do things with you. That works out perfect if you like to do things with other people like I do.

It also gives you another brain to come up with cool ideas of places to go and things to do. It gives you access to new friend groups too.

While we were together I think one of my favorite things we did was going to the Greek Festival in Charlotte.

  • We tasted some wine
  • Looked at art and crafts
  • Saw some traditional performances
  • Ate gyros

After we left we actually walked through one of the surrounding neighborhoods to one of my favorite wine bars ever, The Wine Loft! (I really like wine.)

A perfect date if I do say so myself!

She helped me grow as a person and really zero in on what I wanted in a relationship

This one is gonna sound like a back-handed “pro” so I apologize for that in advance.

When I first started dating, which was basically freshmen year of college, I thought that my goal should be to find someone to marry as quickly as possible. Cause that’s how you win the game right?

I didn’t even consider that just because a girl and I were compatible on a few dates, that marriage was not the next step. Movies about dating really messed with my head I guess.

Debrief: My First Real RelationshipMovie Tangent: In the movies they go on a few dates, have fun, have a fight, “break up” for a second, get back together, and then they are walking down the aisle. The issue is that the movies never show you how much work goes into those “commas” that separate the main points they show you.

Why you playing games with me like this movies???

Movies taught me a lot of what I know about dating so I didn’t know any better.

Anyway through some intense introspection I realized that my dating career should not be a sprint to the marriage finish line. No shade to my married people but that ain’t for me. I can’t even commit to breakfast in the morning.

When we were randomly talking about marriage over dinner I told the girl I was dating that I didn’t see myself getting married until I was 30 and she mentioned she thought she would be married in 2 years…

…the rest of dinner was very awkward and we broke up in the next week or two.

The good thing about this though is that it made me realize that I need to be looking to date people that are on the same page with me on the whole marrying and settling down thing.

I can’t do either one right now. Actually I’m not sure I ever want to FULLY settle down.

Break-Up was not that bad

Like I was saying in the point above, we both realized that we wanted different things. This made the break up more of a mutual thing. I think we both realized over that dinner that we weren’t going to be together for any extended period of time.

I had thought that from the beginning so…

…for me that was not really an issue, but for her that was a deal breaker.

Still don’t think any of us were at fault. Also, from what I’ve heard about other break ups I think ours was pretty cordial.


4 Reasons People Want to Label Relationships

Cons of My First Real Relationship


Dating is crazy expensive. It was so expensive that it had its own separate heading in my budget, like food and gas. My gentlemen will definitely get it, and its 2018 so some of my ladies will too, but paying for two people to do anything ain’t cheap.

Even once we were officially boyfriend and girlfriend I knew that she expected me to pay for things. She would do this thing where she would ask, “Do you want me to pay for this?”

Ladies, don’t play games with me! I been out here dating a long time I’ve picked up a few things.

Asking this question basically forces me to choose between:

  1. Being a jerk and saying yeah you should pay for it
  2. Just paying for it because there is no other way to respond to that question

I can’t possibly win this game once you ask the question. So for everyone… if you want to pay then pay, if you don’t then don’t, but for the love of everything good in the world don’t ask, “Do you want me to pay for this?”

Side Note: I think I’m gonna have to take a look into this whole notion that the guy has to pay for everything, especially if we are talking about the first date. I don’t even know you I’m not gonna pay for your time. If you would like to get to know me then let’s do it, if all you want is the free meal then keep it stepping.

Ain’t nobody got money for that I’m working part-time!


4 Benefits of Working Part-Time After College

Couldn’t flirt with other people

I’ll admit that this is a weird one and it makes me sound like a player, but let me explain.

Before this relationship I was single for almost 22 years. If I ran into an attractive girl that I thought liked me it became second nature to start flirting. Why not right?

I legitimately don’t have to think about it at this point.

On the one hand I am usually looking for someone to talk to, and on the other flirting is fun even if it doesn’t work out.

Being in a relationship put me in the very new position of having to tone my flirting down. My ex-girlfriend very easily got her feelings hurt when she thought I was flirting with other people. Even once I began making myself more aware of it I noticed that she didn’t really like me making jokes with attractive waitresses.Debrief: My First Real Relationship

I do understand how it could have made her uncomfortable, but I want to date a girl that sees me talking to the waitress and gets in on the joke. Someone that sees me talking to a girl at the bar and thinks, “No worries, he’s mine.”

I came here with you be confident in the fact that I am not going anywhere, and if I do want to leave I’ll tell you.

Living Arrangements

There are a good amount of benefits to moving back home after college, autonomy and privacy are not on that list. We always had to figure out our families’ schedules before we could decide to go to our houses.

If our parents were having a get together or didn’t want people to come over than that trumped all of our plans. There was never any chance of an impromptu meeting at either of our houses so we ended up going out a lot…

bringing me back to my point about how expensive it got.

Not only did we not have our own place, we also lived like 45mins away from each other! Now that doesn’t sound horrible to put it in perspective everyone I’ve “talked to” has lived within 10 miles of me. So it’s far ok!

That’s almost 2hrs of commuting every time we went to each other’s houses.


5 Favorite Things About Moving Back Home

5 Least Favorite Things About Moving Back Home

We Aren’t Friends Anymore

It has long been one of my rules that if I date someone and it doesn’t work out I am not going to put myself in that awkward place of still being around them all the time.

It’s real hard to be friends after being in a relationship. Low-key it is hard to be friends after going out on a few dates with someone… sigh, but I’m working on it.

Usually I distance myself and say something along the lines of yeah we might be able to be friends at some point but certainly not right now.Debrief: My First Real Relationship

I go into this more in the article Get Over Your Break-Up the Right Way, but I think that if you don’t get that time away from each other, either you start trying to get them back or someone gets hurt seeing that the other person is not taking it as hard.

Either way there needs to be a break so that feelings can heal and you can more objectively answer the question, “Can we still be friends?


4 Reasons People DON’T Want to Label Relationships

Gift Giving Guide for Every Stage of the Relationship

Closing Thoughts

I think we both thought we could change each other. She thought she could get me to settle down and I thought I could get her to be more free. We liked each other, but…as cliché as it sounds… we wanted different things.


Get Over Your Break-Up the Right Way

My Stories: Wait, She Took My Notes???


Well if you didn’t know now you know!

Sheesh this was a long one! I try to be completely honest with y’all when I write post like this so that you can learn from the stuff I’ve gone through. Don’t make my mistakes copycats make your own!

So let me know in the comments: Do you like posts like this? How was your first relationship? Did anything crazy happen during your first relationship ever?


    1. Crazy Expensive! I was actually just talking to one of my friends earlier about that! Do you think think that has ever stopped you from dating? Yeah me too!!!

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