
It's really down to personal preferences. So I'm gonna talk about mine, hahaha.
I've done it both ways, and like others had both success and failure with both - failures including a spontaneous character relationship that fizzled out and got stale after the initial IC fuzzies but the other player wasn't willing to "let go of something we'd worked hard on" despite the fact it was boring us both to tears so I had to go over their head on it and have my character break up with theirs; and a planned character relationship where the characters didn't get along as well as we'd thought they would (one character was refusing to open up about their common ground with the other, the other was refusing to comprehend that the first could understand their life enough to share in it) and we decided to leave the IC failed romance attempt as an IC failed romance attempt instead of taking it further. (Which, I mean, is still good roleplay! Just not romance RP.)
Both of my character's current relationships were sorta planned, but it was - you know - planned, in that we made a plan, we didn't just say "that's gonna happen now" and smush our characters together. We had the mutual "our characters would be cute together", went over discussing OOC some of their themes and personality traits and seeing if we thought they would like each other, did a few litmus roleplays, agreed it was probably going to work, and went more spontaneously from there - using the mental list of common character themes to guide the relationship's development over time (e.g. both characters have a fear of abandonment? How would they handle it if they were separated by circumstances for a bit?).
I don't think I've ever done this with a total stranger, but I don't imagine the process would differ very much... OOC (for want of a better word) ""interviews"" and platonic litmus roleplays to see if things were going to be interesting, discussing common character traits and themes, before launching into it IC and seeing how things go.
There are a few other characters that mine has spontaneously developed a crush on at the moment, but as someone with anxiety I've found it difficult to do the "my character likes your character, what should we do" conversation. At the end of the day, it doesn't hurt my character too much for the crushes to be apparently unrequited - it's quite IC for him in some respects - so at least there's no harm in me letting it hang like that while I sort out my confidence...
I've done it both ways, and like others had both success and failure with both - failures including a spontaneous character relationship that fizzled out and got stale after the initial IC fuzzies but the other player wasn't willing to "let go of something we'd worked hard on" despite the fact it was boring us both to tears so I had to go over their head on it and have my character break up with theirs; and a planned character relationship where the characters didn't get along as well as we'd thought they would (one character was refusing to open up about their common ground with the other, the other was refusing to comprehend that the first could understand their life enough to share in it) and we decided to leave the IC failed romance attempt as an IC failed romance attempt instead of taking it further. (Which, I mean, is still good roleplay! Just not romance RP.)
Both of my character's current relationships were sorta planned, but it was - you know - planned, in that we made a plan, we didn't just say "that's gonna happen now" and smush our characters together. We had the mutual "our characters would be cute together", went over discussing OOC some of their themes and personality traits and seeing if we thought they would like each other, did a few litmus roleplays, agreed it was probably going to work, and went more spontaneously from there - using the mental list of common character themes to guide the relationship's development over time (e.g. both characters have a fear of abandonment? How would they handle it if they were separated by circumstances for a bit?).
I don't think I've ever done this with a total stranger, but I don't imagine the process would differ very much... OOC (for want of a better word) ""interviews"" and platonic litmus roleplays to see if things were going to be interesting, discussing common character traits and themes, before launching into it IC and seeing how things go.
There are a few other characters that mine has spontaneously developed a crush on at the moment, but as someone with anxiety I've found it difficult to do the "my character likes your character, what should we do" conversation. At the end of the day, it doesn't hurt my character too much for the crushes to be apparently unrequited - it's quite IC for him in some respects - so at least there's no harm in me letting it hang like that while I sort out my confidence...