Advice Column: Response to Stuck in High School

Dear Hailey,

I have been feeling like I’ve been at a cross-roads for about 4 months now. I’ve talked it with my therapist and all of my friends and family and nothing is helping me find an answer or even feel better about the situation. 

When I was in high school there was this guy that I was absolutely in love with. We never dated, or even did anything romantic whatsoever, I just had an insane crush on him for my entire Junior and Senior year of high school. I am 90% sure he liked me back too, but we were both very shy, awkward teenagers and we were both very afraid to tell each other. Me being a teenage girl, I thought (and was told by many) that if a boy really liked you, he would tell you. So I waited and waited for him to tell me and by the time I felt like I should be the one to say something, we were seniors and I was very scared that it was too late (even my friends said it was old news and I was way too late to tell him). Then he committed to go to a college on the opposite side of the country from me, so I felt even more stupid for telling him I had feelings for him and thought that I should just move on and find someone else and that college would be filled with new people and new experiences. 

Starting my freshman year of college, I still couldn’t stop thinking about him. I went so far as to unfollow him on social media so I would force myself to forget about him and not see what he’s doing anymore. Shortly after that, I met my now boyfriend. I didn’t really want to get into a relationship right into college, but it just kinda happened. Now fast forward I’m a senior in college and me and this guy have been dating for 3 years. 

Although I was/am extremely happy with my current boyfriend, I always thought that not confessing my feelings to the high school boy would be my biggest regret in life. I even kept thinking to myself, “I wish me and that boy would have dated, even though I’m happy with my current boyfriend now”. All in all I feel like the first 2 years of my relationship with college boy this was no more than just a passing thought.

However, ever since we started quarantining in March, it seems like I now think about the high school boy at all hours of the day. I had to live and quarantine with my boyfriend in March and April and I remember feeling so guilty when he would tell me he loves me since I would be secretly thinking about a guy that I never even dated 24/7. 

My boyfriend is a year older than me so he graduated in April. He is currently working a job in his hometown. His hometown is 5 hours away from where I go to school so this is our first time being long distance. He drives to see me every three weekends. My hometown is only 30 minutes away from his so when I’m home for breaks we see each other a lot more. My boyfriend is a very sweet guy, he cares about me a lot, we never get into fights, and he always tell me about how much he wants to be with me for a long time. When we are together it is great, and I am happy with him. But I’m not sure if I’m happy to see him in a romantic way or that I’m just glad to see a friend of mine. This is my first serious relationship and I’m just not sure if I’ve outgrown him and it’s time to move on, or if I’m just comfortable and this is what happens when you’re with someone for a long time. I remember the last 2 years of our relationship thinking “I wouldn’t really be that upset if we broke up,” or, “sometimes I wish he would just break up with me.” 

I can’t help but think about what dating other people would be like, specifically this high school guy. I always wish that I could go back in time and tell this guy I liked him when I was 16. Or I wish that I could look into a crystal ball and see if I left my current boyfriend and tried to contact this high school, would it work out? I’m not going to contact the high school guy while dating my college boyfriend though. And we haven’t spoken since Graduation so it would definitely be awkward to reach out just as friends. 

Overall I just don’t know if 1) I’m only feeling this way because of being long distance with my boyfriend, since I am a lot happier with him when we are together. 2) If I should even break up with my boyfriend or not (my parents love him and told me I should stick it out until we no longer have to be long distance, of course my parent’s don’t know about the high school boy part of this story), 3) if I break up with my boyfriend who treats me so well, will that become my new biggest regret in life am I giving him up because I can’t stop thinking about someone I haven’t seen or spoken to for 4 years? and 4) even if I do decide to break up with my boyfriend, is this high school guy someone I should pursue? Is this longing I have for him fate or just me fantasizing about a perfect imaginary boyfriend? 


Stuck in High School (SIHS)

Dear SIHS,

I would encourage you to think about these two issues as completely separate from the other. Your current boyfriend, and this high school guy. 

In high school, life was simple. Attending class, finishing homework, and boys, were basically all there was to worry about. Now you are a full blown grown up. You are close to finishing a degree, you are in a long-distance relationship, you have bills, and life has gotten real. It’s safe to say that life is more complicated now. Your subconscious is trying to tell you something, but it’s not about your high school crush. 

It’s quite possible that you miss the simplicity of your life in high school, and this is why he is constantly on your mind. Maybe there is something about yourself or your life back then that you want to bring into the present. There could be a risk that you wish you would take in your current life, and you are being reminded of a time when you did put yourself out there. 

With your current boyfriend: All of the points you have brought up are valid. Long distance is hard, and completely changes the dynamics of a relationship. You mentioned that you are happier when you are together, and that definitely needs to be kept in mind. Consider if this is relationship is something you are willing to fight for. If you are already feeling lukewarm about the whole thing, that could be a warning sign. Also, think about if this is a man that you would like to spend the rest of your life with, grow old with, and possibly have children with. 

Some other things to consider: Are you connecting on more than just a surface level? When was the last time you laughed together, and spent time together that wasn’t just hanging out while you scrolled on your phones? When was the last time you went on a date, or confided in one another? If you are and you are still feeling this way, that is not a great sign for the future of the relationship. If you aren’t, that could be part of the problem.

It sounds like this feeling that something is not quite right and that something is missing has been present for a while. However, I would be remiss if I did not mention this: With the stress that the world is under right now in a global pandemic, quarantine and social distancing requirements, and other chaos, mental health concerns are even more prevealent than ever. Mental illness can cause discontent in relationships, ranging from minor to severe. If this is something that you are experiencing then speak to your therapist about the effects it could have on your relationship.

These are good topics to discuss with your therapist as well.

Again, I would caution you against breaking up with your boyfriend to pursue your high school crush. It’s really easy to get caught into thinking that a new situation will be better, or that the “grass is always greener”. It’s also really easy to fall in love with the idea of someone because an idea doesn’t disappoint us, is perpetually romantic, and an idea is perfect. However, an idea is also unattainable because people by nature are imperfect and flawed. It is also important to consider how much you have changed since high school, and how much your crush has likely changed as well. 

I wish you luck with your decision. It’s not easy to confront and analyze deep thoughts, or make big decisions regarding relationships, and I appreciate and recognize that amount of consideration that you have put into this. 


Posted in Q&A

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