I am a male student who has been an introvert almost my entire life, and not having many female friends. Currently, I’m in college and due to the nature of my course, I did not have the chance to meet many other female students.

I have been using dating apps for a while now in order to connect with women and maybe in the hopes of looking for my special someone. After meeting a few of them, they told me I am at most friend material and not boyfriend material, because I was insensitive, opinionated, arrogant, defensive, intimidating.

These are just some terms off the top of my head, and some of the reasons why people might think badly of my character or conversational skills. If I were to reflect and rigorously categorize how I could improve my character and conversational skills, it would be in terms of the following:

1) Relevance of my content to the topic

2) My bias and openness to different point of views to the topic

3) My tone, in the post’s context, my texting tone

I have accumulated this feedback from previous mentors who have assessed my spoken skills before, but only for a short period of time. I believe these flaws of mine account for different proportions of why someone do not like to speak with me, but I did not manage to estimate the proportions, which problem I should prioritize to fix, and how actually to fix each one of them.

Giving this in-depth analysis to anyone in a casual chat with me will likely scare them off. Regardless of which, I tried to fish out examples of certain topics which gave them those impressions of me. Many said that my replies were intimidating and it seemed like I always have something to reply to, and that will leave them speechless. My side of the story is that this arises partly from the nature of dating, which is dominated mainly by a virtual texting component, especially so for my country, Singapore. For this post, I will focus on the virtual interactions.

Before we go on a physical date, women prefer to chat, mostly via text, for a relatively long period of time before meeting up, for a minimum of 2 weeks. The frequency of the chat is rather active, adding all the random intervals of time in the same day will get me around 3 hours. If we do not have common topics to chat, a lot of small talk gets involved. My personal policy for these chats will be generally to reply by the minute if I have the ability to, if not by the next time I’m free which should not be longer than 2 hours. Not to say that my texting skills are great, but generally speaking, I think women in my country are not good texters. They often take on the role of a responder, always waiting for men to initiate topics and let them do all the questioning, not even taking the opportunity to ask “How about you?” after they are asked a question.

I think that the “What do you do in your free time?” question pops out a lot in getting to know each other, so I’m going to use this as an example of a small talk question. In response to this question, some of them will try their best to hold the conversation by giving longer replies, which I really appreciate because they give me more personal information and fuel to carry the conversation. Most of them will just say something like “I like to eat” and “I like to sleep a lot” and I eventually run out of things to say if the conversation really stayed at just food and sleep. Even if I had a lot of fuel from the earlier conversations, my fuel is somewhat finite and I have trouble sometimes maintaining “3 hours a day” for at least 2 weeks.

In a desperate attempt to drag the conversation of the current topic, I force replies to “dead statements” like “I like to sleep a lot” with a comment, for example “Wow you must have some really sweet dreams”. Bonus if the comment ended up to be some kind of tease that acts as additional fuel for me, but I can’t think of a particular good example to illustrate what I mean by a tease. Usually I don’t expect a response from this comment, and proceed to ask the next question to expand on the current topic or switch the topic, if either were possible.

Snippet of text which may reflect my problem

Here is a transcript which is said to reflect my problem, and possibly containing a comment that has gone wrong, according to one of my female peers, call her B. The whole conversation started as a rant about another woman I met elsewhere who told me it was difficult to chat with me.

Me: //Rants before this snippet ...

Me: I wanted to ask, after talking to me for “not a very long period of time”, do you find me a bearable person?

B: Hmm, I can say you have your own thoughts, but it’s quite unbearable for me. I mean, as a friend, I'm willing to listen to you talking or ranting or just giving out your opinions in stuff. But as a bf, I don't think I can stand listening to something that make me intimidated like talking to a robot.

Me: Thanks for your thoughts, I did hear this from others as well. I don’t really know how or where I did wrong about the ranting or how I can “cut short”. It doesn’t feel like myself that way.

B: Yes, I understand. What exactly is the impression you want people to see from you?

Me: Ideally I want people to see me for who I really am, because even if I can fake up a good person in the virtual texting world, the real me will disappoint others. But I know that many can’t tolerate my kind of person, so I’m trying to improve. I just don’t know why I keep giving people this intimidating feeling.

B: Would you want to guess what it is?

Me: If I could guess, I won’t ask. Maybe it’s the way I try to push a conversation, when we really don’t have much in common. All girls talk about shopping, travel or food that contains too much sugar, then I become speechless. I think I’m too judgmental also, and reply too fast. I have something against being silent as “it’s bad to ghost” and can’t really flirt like other guys. Maybe I think I’m different from most guys but actually I’m making the same mistakes.

B: I think not being to flirt is okay, replying fast is a good trait. I’ve met a lot of guys like you. Being introverted is very normal, now people are learning how to talk to them. My sister is almost like you, only difference being she's not into tech. In my opinion, I think you're too proud. Proud of being you, proud of being the introverted smart guy, and since it is not normal among other guys, you think this makes you a bit special.

Me: I get that too from other people, just I don’t know where and how those vibes came in. I never boasted about my achievements and I actually don’t have much to be proud of. I make a conscious effort to avoid the red flags other guys do, but it’s quite tough.

B: I think you just never learn. You're too privileged, you know how people think about you, and yet you never change. If you want people to see the real you, then you should expect the same result like the rest of the people you’ve met before. Unless you're lucky enough to find the person who can accept you the way you are.

Me: I think it’s not that I know how people think about me. It’s like similar to this analogy of me contracting COVID-19, touchwood. Everyone is telling me I have it based on a possibility that I’m linked to a previous patient medically proven to have it, but how do I cure something I can’t even be sure I have.

B: You could always take the medical test to prove that you don’t have the virus.

Me: I hope you do know that the test conducted by the clinics is not exactly accurate. There’s a lot of false positives and negatives and the doctors may not be too sure of it themselves.

B: Could you see the problem now?

Me: My problem of being defensive and argumentative?

B: Yes, you always have something to reply. I was so impressed by you after you talk about how in texting, each party have equal responsibilities in keeping the conversation interesting or on going, but that’s just my opinion. Sorry, a girl sees every detail seriously.


What I’m saying is, a "wrong comment" will appear when I least expect it to be, especially when there are progresses in our conversation. The topics become deeper and the replies may turn out to be really subjective and reflective of one’s values. I am not that good in simplifying my thought process into precise and concise sentences, and the end product of a failed attempt will turn out pretty “naggy”, like how this post looks now. Due to the nature of my texting environment, the “dead statements” occur to me quite often, either because we don’t have much in common or that the conversation was really starting to go dry. These frequent “dead statements” caused me to give my comments, which in high volumes will one day give off the vibe that I am “insensitive, opinionated, arrogant and defensive”.

In my defense, I’m really trying to carry the conversation in hope that the conversation does meet the quota, and I have a chance to physically meet with these people to have a real connection, with facial expressions and body language etc. In a way, these comments are a “necessary evil” for me to achieve my goals. Now that this has become the very reason why no one might like to converse with me, I am feeling a bit conflicted on how to amend my chatting behavior to achieve the same goals. My male peers who have known me for a long time, do not find my chats problematic and in fact like me for my liveliness in chatting frequently.

Can someone advise me, how should I attempt to change my texting habits to achieve the best of both worlds? To not be seen as a “insensitive, opinionated, arrogant, defensive, intimidating” person while talking frequently enough to meet people. From my perspective, I recall hearing “insensitive” the most, so on the assumption that every person who commented agrees that my tone is the main problem, I will like to prioritise addressing this. That being said, I’m open to listening to solutions to help me improve in all 3 areas as previously stated.


  1. I mentioned "2 weeks", but this information holds true only before the outbreak of COVID-19.

  2. Most other women I’ve chatted with will not volunteer to reproduce a snippet which showcased my weaknesses, and this friend, although she volunteered to help, did not bring up a previous snapshot, but we accidentally created one while discussing my problems. She’s not a Singaporean, but she’s working in Singapore. Hence the language of the text, is mainly in Singlish and her best standard of English, in text form (with improper sentence stoppages, grammar errors and texting shorthands). I tried my best to fix them to basic English and merge them by speakers to make it more reader-friendly, but since they’re processed 2nd hand, the nuance of it may not be completely captured by me. It will also be intrusive to ask her to clarify what she meant.

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    Do you chat in English? If so, could you post a transcript of one of your chats that you think is problematic? That would be easier to give advice on than your abstract description.
    – Kat
    Commented Jun 6, 2020 at 5:57
  • This is far too vague to be answerable right now. Can you give a concrete example of a chat?
    – user141592
    Commented Jun 6, 2020 at 8:13
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    I have uploaded a transcript of a potential problematic chat. Feel free to request for a format fix as I'm not used to posting on this site. Commented Jun 6, 2020 at 8:29
  • Good question with examples! It's good that B told you immediately when you got wrong (when she said "could you see the problem now?", it means, and I agree, that your previous statement reads as condescending. I can't write full answer, so I'll just put this in a comment, but as a hint, it can be rephrased into more casual like "Oh, but isn't the test sometimes faulty? Based on what I read, there are false positives.").
    – justhalf
    Commented Jun 7, 2020 at 13:43
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    Hmm, that's obviously translated, so it's still difficult to give meaningful feedback, especially if the issue is your tone or wording. I also suspect "intimidating" might not be exactly the right word to describe how people are perceiving you. Based on the context, is it possible they mean that you dominate and control the conversation? Maybe you spend a lot of time espousing your thoughts and opinions but you don't make the other person feel listened to? If that sounds like it could be accurate, I can post an answer of how to address it.
    – Kat
    Commented Jun 7, 2020 at 20:33

2 Answers 2


I may be wrong here, but I see in your responses a pattern of needing to share your opinion on everything, and needing to be right as well. Let me offer you some words you could use in response to things a person tells you over text:

  • tell me more
  • what's that like?
  • sounds great
  • good idea
  • you're right

This gives the other person a chance to feel like they are interesting and important, as opposed to their role being to read your speeches on what the world is like and how things should be.

You say that some of the people you talk to will only talk about boring things like food and sleep. I wonder if they feel safe discussing other things? I know a young man who comes to some of the same parties as me and consistently spends the entire party telling people You're Doing It Wrong. As in "you took the wrong thing in university", "that was a terrible place to buy a house" "this is not a good time for you to be having a child" and so on. Yes, out loud, to people he just met or knows only slightly, with other people hearing. I hope you are milder than this person. No matter how mild, people don't want to be wrong. They want (as you do) to be interesting. If they read a long rant from you about some other person, they may rightly worry you would rant about them like that. If you type a lot about yourself, or your thoughts about what they just told you, they don't feel interesting.

So ask them crisp and specific questions. It's ok to start with something fuzzy like "what do you do in your free time" but then react to what they tell you. Ask more. Sometimes vague things like "tell me more" or "what's that like?" but more often, a followup that asks about one aspect of what they mentioned.

If they tell you they like to eat, ask "what kind of food?" or if that's obvious from your culture, ask them to name something delicious they've had lately. Ask if they cook at all, if they prefer to stop by a street stall or go somewhere and sit down. Suggest that perhaps sometime in the future the two of you can eat together at one of those places. Ask them if they could travel somewhere far away, where would they go, what kind of foreign food interests them, and so on. Ask if they watch cooking shows or follow any foodies on social media. When they tell you they like something specific, if you like it too then say so! "Oh, yes, that is one of my faves too!" or "Oh, yes, I love to make that!" If you don't like it, don't tell them so, just keep asking more things.

If they tell you they mostly just sleep and eat, you might say something like "it sounds like you don't get a lot of free time for hobbies. What would you like to try if time and money were no object?" You could then give an example like skydiving or learning to play an instrument or some other thing you wish you could do but haven't yet. When you give information about yourself, keep it short. "I would love to try sailing one day", not a 15 minute speech about how boats work, why you want to sail, why you haven't yet, and all of that.

I would also encourage you to think less about the conversations and more about the woman you are starting to get to know through these texts. What is she like? What would it be like to go to dinner with her? What would it be like to date her? It's ok if you feel she is shallow and uninteresting, and the two of you agree to stop texting. That gives you more time to spend with someone who you want to learn more about and want to spend more time with. That's the point of these conversations, after all.

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    You can see a great example of this if you read the other person's texts. "B" asks questions to get OPs thoughts multiple times.
    – Kat
    Commented Jun 8, 2020 at 6:15
  • Hmm, I like your suggestions on how to expand the conversation as a questioner, but I wonder if conversations like “What would you like to try if time and money were no object” kind of questions really works? It feels like those “If you can have a superpower, what will it be” kind of questions, which feels strange in a conversation in my opinion. Commented Jun 8, 2020 at 11:56
  • If I understand correctly, you’re trying to suggest a guideline of “When you give information about yourself, keep it short”, and this is in response to someone’s question, and hoping that they will ask another question about your response so that you could expand further. If I’m the questioner, and I give a question, they respond and ask “how about you”, and I give my reply, would you recommend waiting for their next question or try to ask another question next? This is where I find it conflicting whether I should offer more free information for them to ask more questions or just wait Commented Jun 8, 2020 at 11:57
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    There isn't just one kind of question you can ask. Some are crisp yes/no things, some are vague. Some invite expansion on what was just said, some change the subject. Some are you-based (I love X, have you ever tried it?) and some are them-based (what is it you love about Y?) and some are in between. As for keeping your answers short, that's so the other person has some input into the conversation. They don't want to passively listen for 15 straight minutes to your opinions. They want to at least say "really?" or "what happened next?" or "is that difficult?" once in a while. To be involved. Commented Jun 8, 2020 at 12:03
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    I think while you’re right to think that one should focus on the bigger picture of assessing whether one is a good fit for a date instead of thinking about the conversation, I think thinking about improving conversations helps to better sieve out a person who is a good person but only bad at texting. From my experience there is no hardly anyone who passes the normal standard of being “unshallow and uninteresting” in text, but I need to talk longer until they feel more comfortable to do better, so there’s no escaping bad conversations. Commented Jun 8, 2020 at 12:07

Reading your conversation, there is a small thing that sticks out for me, even though you don't seem to focus on that. B says

Hmm, I can say you have your own thoughts, but it’s quite unbearable for me. I mean, as a friend, I'm willing to listen to you talking or ranting or just giving out your opinions in stuff.

and later you say

I hope you do know that the test conducted by the clinics is not exactly accurate. There’s a lot of false positives and negatives and the doctors may not be too sure of it themselves.

which is what escalates the situation. It seems with this limited scope of view, that you are fast to voice your opinions, that might be controversial. Your statement regarding the test seems absolute and does not invite any discussion. Nevertheless, there are surely people that don't agree with you on this topic. Stating controversial things as facts, especially in a dating situation can be a turn-off. If I don't agree with you that is fine, when we can agree that we don't talk about it or if you are open to hear my opinion and rethink your position. But your statement, given the context of a well meant metaphor, shuts the conversation in this direction down and also is voiced in a lecturing way. To be honest, I would not really want to continue this conversation afterwards.

As we can only see a small conversation snipped, this is of course highly speculative. You could scan your conversations to make out situations, where you voiced an opinion about things that you know others may seem differently. If this is the case, I would suggest you think twice about telling your new aquaintances about your opinions on politics, religion, money and topics that others may seem as conspiracy theories. That is a general advice for conversations with (nearly) strangers or in the workplace setting. If you are unsure whether your opinion falls in the latter category, google it. If there are any news articles connecting your opinion with conspiracy theories, even if you don't agree with the source or think it is not trustworthy, it is better to keep your mouth shut about it until you get to know the other person better. This will prevent the other person from jumping to conclusions about your attitude about certain topics before they know you enough to understand your reasoning.

As requested by OP, here is a section about how to voice these opinions in a more inviting way:

First of all, I want to reiterate that in an early stage of any relationship, regardless of it being friendship or love, it is wise to avoid the more controversial discussions until you get to know the other person, know what are hard limits for this person in regards of certain topics and know how a discussion with this particular person can be performed in a pleasant way for both of you. An example might be, Person A is pro life, but person B has had highly negative experiences regarding this topic and therefore will shut down in the moment person A mentions this topic. Due to personal experiences, it is highly unlikely person B will change their view and might resent person A for not agreeing with them after such a discussion. In this situation, it would be better if person A got to know about person B's troubled past and then decided it's best to spare this specific topic in conversations with B.

If you want to have a discussion about a controversial topic as an intesting conversation, try to state your opinion not as facts, but as what you've read/heard/seen. As an example, you could have said

Unfortunately the metaphor does not work this far, as I cannot test myself like you can test for Covid-19. Also, I have read in [newspaper] that these tests are not that accurate, so I don't know if it would help.

B can then answer

Oh, I've heard about this article, but they got their numbers wrong. [other newspaper] cited a study that shows most test are pretty accurate.

Or they might answer

Oh well, maybe we should use another metaphor then. Maybe it is for you like when...

This way you are not discussing your believes, as we all know it is not easily possible to change what a person deeply believes, but you invite the other person to discuss sources on a scientific basis. The good thing about this is, if a source is wrong, none of the participants needs to be insulted, as this can be objectively proven and does not belittle one of the participants knowledge or believes. It is easy to say

Oh I didn't know this source, thank you for pointing me to it

and hard to say

Oh I see, I was wrong the whole time.

Note also that the first sentence also does not tell the person they are wrong, but admits a mistake on your side to choosing the not quite fitting metaphor and helps to phrase what you actually want to say. If the other person has no interest in discussing scientifically about the controversial opinion, they can also chose to find a better metaphor for you to understand you better.

So to wrap it up:

  • don't state your opinions as absolute facts but invite a discussion by sharing your sources
  • Offer another path the conversation could take by adding another part to your answer that does not include your opinion but is on topic for the previous conversation (in your example, the conversation was actually about you being hard to talk to, not about COVID-19 tests)
  • If the other person engages the discussion and disagrees with you, don't try to "win" the argument, but actively try to find out why the other person believes their point to be true. Ask questions and most importantly listen and don't shut them up.

Here is an article about "arguing with people you don't agree with", you can also google that phrase, there are plenty of tips out there.

  • Thanks for your answer. I agree with you that I have a tendency of having views that are not supported by evidence or might be considered controversial, and my tone is not exactly reflective of the fact that I know that’s the case, and hence shuts down the conversation. The problem I experience is that my conversations often lead me to a stage where I need to say something that is unsupported or just shut up and change the topic, which causes conversation to die either way. Do you mind sharing how I could improve my tone so people will know that I know I’m making an unsupported opinion? Commented Jun 8, 2020 at 11:39
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    When I have some thought or feeling that I'm not sure if it would be successfully communicated in my tone, I just say it explicitly rather than relying on tone (e.g. "by the way, I'm not sure if my tone shows this, but how I'm feeling about this is X."). For this specific example, if I really wanted to share an unsupported opinion, I might preface it with "I want to share an opinion of mine that I know is unsupported/not well supported". I would also add "... so I understand if you think it's not a good reason/argument", to communicate that I'm not assuming they should agree with me.
    – rayna
    Commented Jun 8, 2020 at 18:03

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