Over Stepping Boundaries

A story about a teenage boy having an emotional affair.

5 min readSep 20, 2018

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Boys. Single Boys. Boys in relationships. Are they really any different in the eyes of an infatuated girl? To what extent is it acceptable to try our luck?

My mother gives the best relationship advice. Probably because she had lots of boy drama and dysfunctional relationships before she met the darling that is my father. I not so recently went to her a with an issue that I had mixed feelings about. I was falling for someone who was in a relationship with someone else. And I thought he was falling for me too.

‘’ What he does to her, he’ll do to you,’’ she said to me.

If he’s giving you the impression that he likes you, when he’s with someone else, this in itself is a sign of his dishonesty, disloyaltly and unfaithfulness. It’s like hes cheating on her emotionally, an emotional affair. Telling her one thing to her face, but telling me another. Do I really want to be with a guy who tells me he’s got feelings for me when he just got into a relatively new relationship? What does that say about him?

Him and I were friends for a long time. We’ve always had that flanter (flirty banter) going on. And he always said that we always had the worst of timings. Either he liked me when I didn’t, or vice versa. And he was right. Because it wasn’t up until he started going out with his current girlfriend that I realised I might want more than being just friends. He chased me for a whole summer, asked me out to dinner, drinks, you name it. But I just wasn’t into it. He was too over the top for me. Super into cars, only wears designer shirts no matter the occasion. Likes fancy dinners and expensive wine. And as much as I love all that too, I love it on special occassions. When you do something special, often, it loses its meaning. As attractive as I did find him, I just didn’t see myself being happy with him for long enough.

I always felt like he’s the kind of guy who just needs to have a girlfriend at all times. Not only for emotional companionship and someone to lean on and talk to 24/7. But to have someone to spoil and spend money on. Someone to post on social media. Someone to take to events. Do I even want to be in a relationship based on these reasons?

After ending a 3 year relationship, and a failed attempt at starting a relationship with me, he got a new girlfriend. A very sweet, intelligent and well mannered girl. A girl who I know, and respect. But when the time came and I started to realise how I may want to be with him as more than a friend, the respect I had for her seemed non existent. I was willing break that respect and try my luck. I thought to myself, Should the fact that the boy I like is in another relationship stop me from admitting my feelings to him? Will that make me an honest person, or a selfish one?

I really wish I had an a solid answer for you. A ‘Yes, go for it!’ or a ‘No, it’s too risky!’ But I don’t. There’s no general rule to follow here. You’ve got to go with your gut and be ready for the humiliation that comes with the rejection. He might chose to leave her and be with you, or he might chose to stay in his comfortable relationship. But one piece of advice that I can give you is that you won’t know unless you try.

So I did it. I told him how I felt. And he was confused. He didn’t know what to do. Take a risk? Leave his girlfriend and try date his best friend? OR Keep things the way they are? Stay in a comfortable relationship based on convenience rather than passion in hope that the spark between them will grow over time.

I don’t want to sound like I’m making assumptions about the conditions of the relationship. I’m just speaking from my point of view. Because in my opinion, a relationship is based on trust and passion, not convenience and secrets. And thats what he had. Secrets. Showing up at my house with ice cream at 10pm, waiting for me outside my office just to surprise me, randomly picking me up from university and taking me on long drives by the beach. And she knew none of this. He’d tell her he was home, or at work, or out with the guys. He even ‘joked’ with me about kicking her out of his hotel room one weekend so that I could be there instead of her. Even worse, he told me he would break up with her as soon as they get back from their holiday abroad, and spent the entire holiday texting me.

But what was I supposed to do? Tell him to stop? Was I really expected to tell the guy I liked to stop giving me attention? I was loving it! But it was self deteriorating kind of loving it. I felt like I was being dragged across the floor from my hair. And this emotional battering made me realise. This isn’t the kind of guy I want. I don’t want someone who texts some other girl whilst sitting across a table from me. Or someone who leaves me in the dark about the emotional affair he’s having. I want someone real. So I cut him out of my life. And it drove him all kinds of crazy. I told him I no longer wanted him. So what did he do? He stayed in his relationship of course. As for his girlfriend. She still doesn’t have a clue.

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Overdramatic Realist. Optimistic and Borderline Resentful Hopeful answers to desperate questions.