Do you have any tips on what to do if I’m interested in someone?

Last night, a student wrote to me, asking:

Do you have any tips on what to do if I’m interested in someone? I’m very scared to come across as too clingy from the start.

Oh, I know how intimidating that can feel!

I think my best advice is to treat that person the same way you would treat your friends. Just because you feel something for that someone, doesn’t mean you go out of your way to do very special things. If both of you haven’t reached a point where the friendship/relationship has grown closer, doing very special couple-ish things at the start can come across as cringeworthy and awkward.

Now the reason why I say you should handle that person the same way you would treat your friends is because that is how you really are when you interact with others. If you change your manner of interaction just for that person, expectations will be set that you are that other person (which you are not). And it can and will be tiring pretending to be that someone that you’re not. So it’s better to be accepted and loved for who you are, rather than to have that someone accept and love a pretence of yourself.

At all times, get a grip on yourself and don’t cave in to desperation or impatience. That’s when we say or do stupid things that will make that person feel uncomfortable. You need to do your best to be calm and confident about it (even if deep down you don’t feel that way).

If you reach a point where both of you are interacting with each other daily with excitement, try to upgrade the friendship to that of a closer friend. Friendships deepen not because of the frequency or quantity of conversations, but from the quality of conversations. Having heart-to-heart talks are good in getting to know people on a closer level and to establish closer bonds. But be careful not to become overly whiny in your heart-to-heart talks about issues. I know some people who degrade heart-to-heart talks into whining sessions about every small problem in their lives, and it becomes a really bad habit (and bad friend) where all they can ever talk about are their problems. It’s more important to engage in active listening so that you can better understand that person (and maybe evaluate whether that person has potential to be a partner and future spouse).

At the end of the day, conversations can only go so far. What you want is to have shared experiences on a variety of matters (applies to friendships too). So don’t just be texting/calling the person only. I know it’s hard to meet up and do fun stuff during this COVID-19 pandemic, but you can always find interesting and creative things to do, so no excuses! Find common projects to work on. Stuff that both of you like to do, or even better, stuff that both of you want to do but have never done before. Do fun stuff, and have fun!

The key is you both want to feel comfortable hanging out with each other, comfortable doing things together, comfortable talking to each other.

Once you find that you are doing these things on a regular basis, it’s a really good sign that the person has strong interest in you too. You can drop your hints of interest (although if the person is perceptive, that person probably can tell from your body language anyway). I don’t want to tell you what to do, because what works for me won’t necessarily work for you. I guess the rule is: Don’t be creepy, and don’t be desperate.

(Personally, I don’t like the rubbish in magazines that tell people to play hard to get. That is just awful advice that advocates manipulation and mind games. I think the only time this may work is if you are interacting with someone who gives off a player vibe or has been going for lots of casual flings. So it might be a test of sincerity. But if that person is already giving off player vibes, it’s a red flag. And I would seriously reconsider. So… Be warned~)

If there’s no hesitation or aversion from the other party, or if that person is smiling like an idiot non-stop at you all the time, then you know all is going well, and you can start preparing to confess. Don’t rush or pressure yourself or the other person. And try not to do overly romantic stuff because it can be very overwhelming for that person (unless you know that person wants that sort of stuff).

You want to give that person the time and space to think and respond to. Some people can’t say yes immediately (not because they don’t like you, but because they are daunted by the idea of taking it to the next level). So if they feel very pressured, they may instantly say no (and regret it) because they can’t handle the pressure. So give them time and space (unless of course you are super sure, and maybe the other party has already been quite explicit in expressing interest in you).

So, all the best and have courage! Let me know when you are successfully attached. If we can meet, I want to congratulate the both of you in person (I really mean it!). :D

Author: Jonathan Y. H. Sim

Jonathan Sim is an Instructor with the Department of Philosophy at the National University of Singapore. He is passionate about teaching and he continues to research fun and innovative ways of engaging students to learn effectively. He has been teaching general education modules to a diverse range of undergraduate students and adult learners at the University.

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