This was a really nice read. Thank you all, and especially thank you @amatt for such lovely insights. I think I need to write that down somewhere as well.

I can understand the need for honesty. I’ve been like that. My mind is quite literal and not following certain rules can actually cause a lot of stress. As an example, my mother has a very selective memory and her storytelling tends to be coloured with a bit of drama, instead of being too involved with the details and whether things actually happened the way she’s telling the story. This has always caused me some mental anguish. She doesn’t understand my reaction to it at all, and thinks that it’s not such a big deal. But that’s just how it goes, and I have to understand that she takes some liberties in favour of dramatic storytelling. Sometimes the truth isn’t what people are looking for and during those times I need to let go of my own obsession with it. I have noticed though that the more I spend time thinking, the more obsessed I get with the truth. The more time I spend feeling, life becomes more balanced. It gets easier to let go of the details and see things in a different light.

There is a danger in having this image of oneself as being “always honest”. Apart from accidentally being inconsiderate of others’ feelings. When we start to believe that we are a particular type of person, we kind of fail to notice all the times when we are not like that. The belief is so strong that any evidence against that would cause a cognitive dissonance. Instead of being able to face the fact that there are times when we aren’t being completely honest, it’s easier to create a justification for why in that particular time we failed to be honest.

Or perhaps the honesty can be a justification for failing to be considerate towards another person. I cringe every time bad behaviour is justified by “being real”. It’s silly. It’s not about being real, as in genuine. It’s about being inconsiderate towards others and commonly accepted social behaviour. So there is a chance that the honesty becomes a justification of an event gone wrong, and was not actually the reason for things going wrong.

I also am not so sure if dating is a game to be played. It might seem like it, but it’s actually not. A person who has their own interests and their own life, has their temperament under control, who is kind and courteous towards others and has a healthy sexual appetite isn’t going to have problems finding a partner. But when we feel like we are lacking in those areas or think that we’re perhaps not as good as we think we should be, there is a temptation to appear as if we’re all that. As an example, you meet a new person, become really infatuated by them, and feel the urge to send them 20 text messages right after meeting them. There’s an inner clash between this strong urge and the rational part that knows that it’s going to appear desperate. If you do end up sending all the messages, and consequently scaring the other person in the process, it’s possible to justify it by saying “I was just being honest about my feelings, and if they can’t handle it, then perhaps it’s better that we didn’t end up together”. Not sending the messages might feel fake and like playing games. “I want to express my interest, but feel like I need to hold back to appear cool and collected.” With some maturity though, none of this would be a problem. With maturity, you can handle the strong urges and extreme feelings. With maturity, things aren’t that black and white anymore, but it doesn’t mean that honesty or being genuine would be sacrificed. Handling emotions becomes easier, so there are less extremes. Even reading social cues becomes easier.

I know all of this is kind of hypothetical, and not necessarily something that is an issue for the OP. I just wanted to point out that things aren’t always what they appear to be, and with some time, patience and growth, a new reality might appear. What you thought was the truth is only a partial truth.