How do I talk to someone I've had issues with before?

Question

Last year a girl I go to school with found me annoying. She didn't have any grudges, it was just "I wouldn't choose to sit next to him." This year she doesn't find me annoying, and I have been tring to talk to her but it ends up being very awkward. I'm a guy, and she's a girl. That makes my various attempts start to look either very desperate or very thirsty. I've been told I'm incredibly engaging to talk to, but finding a topic is really difficult for me.

I'm trying to talk to more people, like my therapist told me to, and I know we have similar interests, but it's very difficult for me. I end up just saying "How's your day been?" and getting an answer I can't really respond to with anything other than "that's good."

I have BPD ⁽¹⁾, if it helps.

How do I start a conversation with her in a way that doesn't look like "another failed initiative"?

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^{(1) Borderline Personality Disorder}

Answer 1

Try to be natural

I've been diagnosed with BPD too, so I totally understand the whole "I'm trying to be nice and coming off as annoying/creepy/awkward/too-intense".

So, my recommendation, take the pressure off the whole situation to be natural.

1. Look for a time in which there is no pressure, i.e. waiting in line for lunch, waiting for the teacher to start class.

2. Approach to her as if you didn't know anything about her. If you haven't had many conversations before, she might be taken aback by the fact that you mysteriously know the topics you have in common, even if your knowing comes from a genuine interest, it might come off as stalking.

The way you state your question may be an additional barrier for you here. Let me explain: The fact that you are starting off from

I've had issues with her

may be making you come off as trying-too-hard. Try to erase that background and start off from zero. Even if she doesn't notice the difference, you will feel more confident.

3. Stay out of personal questions for now, let her set the tone of the conversation for her to feel confident when talking with you. Taking pressure out of the equation, conversations will flow much more naturally for both and that will probably increase trust.

Come up with a topic, not too deep yet, the trust to talk about deep matters comes with time for most people. For example, if you are having lunch, make a witty comment about food. "That seems not-so delicious. Have you tried X?". Try a simple question for a few days, the conversation will grow soon.

Maybe it seems like "How's your day been?" is a simple question, but if you want honest detailed answers, you need her trust first. If she doesn't know where that question came from or she doesn't feel like sharing her feelings/whereabouts, most likely she will opt to answer "fine" or "boring" or something that ends the conversation right away.

You've got this!

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Update: how do you get passed the monosyllabic or vague answers. I would say that the key is to avoid pushing it.

You can try by making more specific questions such as "how did you do on that test?", "Did you feel comfortable during the conference?". If you still get evasive replies, leave it at that, smile and continue whatever you were doing. In another occasion try with a different phrasing.

When someone I don't know very well asks me a question, sometimes I feel exposed (this person whom I know nothing about is inquiring something about me) and that can lead to uncomfortableness. For me, the thing that works best is to show that I'm willing to open and trust by sharing how I feel. For example, "Did you see the new collection on the library? I found this book and really liked it", "I hate assignments like this", "Did you like the conference? I found it interesting". Make it about her but also show that you want her to know you as well.

I hope it's useful : )

Answer 2

One thing that you need to keep in mind is that it's possible that she might not be interested in talking with you even though she is no longer annoyed with you. When I was using dating apps, I found myself not knowing if another person wanted to talk with me or not. What I did to clear up the mystery for myself was to ask a question that opens the possibility for a longer answer. As I explained in this answer

start talking about something that she is interested in, such as the book she's reading, or another book from the same author, the music group/TV shows on the tee-shirt she wears, or the small dance she made. For example, if she was reading a book by an author you knew then you could say something like this.

Hey, I noticed you're reading [INSERT_BOOK_TITLE]. I think she's a fantastic author. How are you enjoying it so far?

You've mentioned that you have similar interests to her, so you can pick one of those interests and ask an in-depth question about it to try and elicit a longer answer. It was my experience with dating that women who were interested in having a conversation would give very detailed answers that would further the discussion whereas women who weren't interested in having a conversation would give a short answer that added no additional detail.

Not only will this approach help you figure out if she is interested in having a more friendly conversation, it will also initiate said conversation. As I mentioned in the answer I linked

I've found that this is the best approach because it creates an active conversation for both parties. When you are attempting to meet someone that you like, it is especially important that they be actively engaged in the conversation, because if they aren't they'll likely get bored and move on.

While that question is about approaching someone new, the same skills apply for trying to start a conversation with someone that you don't have much of a relationship with.