You have just received that “Hey stranger, want to grab a drink Friday Night?” message in the DM and when you open it, it’s from the one and only. Its your high school sweetheart, your crush!
Now you are sweating and cannot breathe. You fall off your chair and need a moment to gather your thoughts. Due to shock, you open your phone again just to make sure it’s them and you reread the message just to be sure.
You are not daydreaming, it’s happening!
Aaaahhhhhhhhh!
Okay now that we have sort of gotten over the shock and we have screamed and jumped up and down, we need to decide whether we want to go with this person or not. You are allowed to call your best friend and let them know that the sky is probably falling because the impossible just happened.
Your dream is coming true and you either saw it coming or you didn’t.
Maybe you saw each other at the high school reunion, and you talked and now he is sending you this message. Perhaps he made the means to get your number on social media and contact you.
Well, we are here now, so none of that detail really matters!
This is a person whom you really liked and now they are somehow back in your life years later. You always wondered where they ended up. Somehow, they pop up on your social media and you spend hours on end going through their social media
Obviously, they have changed but the spark and feelings you once had for them are reignited and you cannot help but wonder if you should go with them for drinks or not.
Although the final answer lies with you, there are a few things to consider which I will point out.
I wouldn’t want you to wake up the next day and regret a one-night stand that could have been avoided with a little more reasoning.
We all know that when it comes to love common sense tends to fly out the window!
Right before we get into the things to consider before dating your high school crush years later, let’s talk about your high school crush. How do you know if someone was a high school crush?
Who is your high school crush?
Be honest with yourself, there is that one person you went to high school with whom you wish you had dated. You were just a child, but you knew that whenever you saw them your heart skipped a beat, and you couldn’t concentrate.
You always wanted them to be your high school boyfriend or girlfriend. Somehow you even remember the first time you saw them (the whole world disappeared, and it was just you and them).
Yes, you were young, but you knew that if that person approached you, your life could have been different. You saw a marriage with this person.
You were sure they were your life partner and one day you would get married, have two kids, and a dog, and move to the best neighborhood where you will live happily ever after.
Your crush filled your dreams and each day you saw them at school your morning lit up.
Crushes come and go but there is one that has stayed the same.
Even if the crush never looked at you twice or greeted you, you still believed that one day you will meet again.
Well, that someday is today, and you have to decide whether to go for drinks or not.
Let’s talk about things to consider before dating your high school crush years later.
Few things to consider before dating your high school crush years later
1. Your crush has changed
It has been a long time since you saw this person and they have changed, but so have you. They may look different and talk differently as well.
We have all been through the covid19 lockdown so yes, we have gained weight. So don’t be surprised if your crush has gained a few pounds.
Some of the big changes could be that they were in other relationships, got married, had kids, and got divorced. The point is your crush’s life has not been stagnant.
From the last time you saw or heard about them, they probably got a new job and moved to a different town.
Be prepared for the changes that have happened in their life.
2. Let go of expectations before dating your high school crush years later
You might have dreamt about what dating this person would be like, but those expectations may not be met, and you have to be prepared to deal with it.
Although this may be the beginning of a new relationship, it’s important to start it on a clean slate with no expectations. The expectations you had of dating in middle school or high school have changed, mostly because now you have a lot more experience in real life than you had as a naïve school child.
3. The reality of actually dating or the idea of dating your high school crush years later
Sometimes we fall in love with the idea of dating someone. So, before you decide to date your crush from high school critically think about it. Do you really wish to date this person or it’s just an idea you are fascinated with?
Sometimes you date someone and only during the time you are seeing each other do you realize it’s not as full of unicorns as you initially thought.
You realize the butterflies you had in your stomach are not there anymore!
Then you have to break things up and admit that you only liked the crush because everyone liked them.
4. Your preference and tastes in relationships have changed
It could be that you wanted to date this person because you thought they were the hottest thing ever and today you realize what you defined as hot in high school does not necessarily float your boat today.
You might have been into smart, nerdy, shy people but now you realize you want someone outspoken, outgoing, and extroverted. You realize you don’t really care whether a person is smart or not as long as they love you and care for you.
Now that you have grown up your list of what you want in a partner has also improved. Now you have financial stability, independence, kindness, and cleanliness at the top of the list.
Does your crush tick any of the boxes you have, or do you just want to date them because the opportunity has presented itself?
Look at how many people were your high school friends that you don’t talk to anymore. Sometimes we grow apart. It’s not that they are bad people, but we can grow up to want different things.
The same thing can be said about crushes.
5. Are you attracted to this person today?
Having a huge crush on someone means you are somehow attracted to this person, but what if this distance and years you have not seen each other lets the attraction fade away. You realize you are not into them anymore.
Be sure that you are actually into this person otherwise, it’s time wasted for both of you.
If there is an old flame to be rekindled do not let this opportunity pass you by, but if there is not even a small spark let it go.
6. Do you (still) connect with this person at a deeper level?
After meeting with this person and having a conversation with them, do you share values and beliefs? In high school, it was just a crush but now you must think a bit deeper.
- What are some of the opinions they strongly hold onto that you disagree with?
- What are some of the common things that both of you like?
- Where are the two of you going in life?
- Do you want to get married or just date and have fun?
- Do you plan on having kids and getting married or having a life partner?
- What is your crush looking for in a partner and do you match those requirements?
- What is their career path?
- What views do they hold about social issues like gender-based violence, unemployment, racism, vaccination, organic food, pets or climate change?
- Do they subscribe to a particular belief system?
Although these questions are not the be-it and end-all, they surely give you an idea of what you are dealing with and if you are compatible for a long-term relationship.
Although it’s a crush maybe it’s an old crush that must stay as a crush and is not worth exploring a romantic relationship with. These are realities that you have to think about.
When you date your high school crush years later and want to date them make sure you are doing it for the right reasons.
Why you should date your high school crush a year later
There is no right or wrong answer but for now, we will explore the positive aspect of dating this person.
1. You know more about them than a stranger
It could be that you know your crush a little bit more so it might be best to explore things with them. Although they have changed, maybe they have not changed that much.
As it is said, better the devil you know than the Angel you don’t know.
Maybe you were best friends with your crush, and you knew everything about them, so they are far from being a stranger. Perhaps you have had mutual friends and you guys used to hang around a lot together in high school.
So, your crush may not be a stranger.
Many of us single people have tried all sorts of dating apps and to be honest, swiping left and right is exhausting. The dangers of meeting unknown people in this day and time are real.
No one wants to be a victim of the Tinder Swindler!
2. An ex-boyfriend who wants a second chance
Some people were lucky enough to have at least dated their crush in high school. I call these people “God’s favorite children” because they wanted something and got it unlike the rest of us.
Anyway.
If this crush was an ex-boyfriend or your first love, then maybe the conversation you need to have with yourself is a bit different. It could be that you tried dating but for some reason or other things didn’t work out.
But now this could be an opportunity for second chances whether the previous relationship ended on good terms or bad terms.
Because you are considering giving it a try, do not treat this second try as a previous relationship. Look at it as something new because there is no harm in reviving former love.
If your crush hurt you, try following these simple steps to forgive them.
After forgiving the crush you can consider dating this high school crush.
3. Give it a fair try
You might be bitter that you didn’t go out with your crush on prom dates but don’t let that cast a dark shadow over this possible new relationship.
Leave the past in the past.
Start with phone calls and a text message or two throughout the day. Dating takes time and you need to be fully involved in it. The terrible thing about not dating your high school crush is living with the regret of not giving it a try.
If you really like this person, give it your all to make the relationship work.
You never know, dating your high school crush years later could mean that you have met the love of your life.
What if I want to date my high school crush years later but I am married?
Dating your high school crush years later can be fascinating but should you even be considering it? Should there even be a small part of you that entertains the idea of dating this person?
If your biggest crush from your teenage years, sophomore year, or senior year of high school comes back into your life a bit too late it can be confusing.
You could feel caught between a rock and a hard place and temptations to explore this new thing might arise. But is it worth risking your marriage for something that might not work? Or maybe it might work, but honestly, we will never know.
Although this might be sad it’s one of those things where you will just have to live with the regret of what could have been and should have been.
You could either spend your whole day daydreaming and wishing things were different or focus that energy on improving your current marriage.
As they say, the grass is not greener on the other side, it’s greener where you water it!
Your true love could be your marriage partner and not your high school crush that wants to go on a date with you.
Do not let a high school crush disturb your peace and happiness, it might not be worth it.
Final thoughts
Whether you met your crush at a reunion or in social circles with other friends, it’s not a bad idea to consider dating them. Or at least consider going on your first date.
Not just going for drinks but a real date where you dress up and explore if there is any romantic interest between the two of you, it might be the best thing you have ever done in your adult life.
Either way, it is said that by the age of 23 most people have met their life partner already even if they don’t know it (whether this is true or not I don’t know).
Although high school years were the best or worst time of your life, dating your high school crush years later may take you down memory lane.
Whether things work out and you go on an actual date with this person or not you can remain old friends.
No matter what happens I wish you a happy ending!
If that ending is you alone do not be discouraged, use this time to take care of yourself and love yourself. Go on solo dates and consider spending time with yourself. Find different ways to meet new people. There is enough love out there for each one of us.
If you are dating a high school crush years later, share with us what your experience has been in the comments section. I love hearing from you!
