First of all, I usually don't post about swim's experiences anymore since I think this site contains many very well written trip reports. However, me and swim don't think many people tried tripping while very sad before, so It might be intresting to other people. Swim did not take any notes during the trip, so the timings might be slightly off and not to many details are remembered.
Situation
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Swim's girlfriend broke up with him about a month ago (after a relation of about one and half year). Swim took LSD since then, but was thinking about his ex-girlfriend a lot that day because he tried to win her back some days earlier. Swim was rather sad, but still decided to take some acid. He took one and a half rather strong blotter of lsd. Swim is a very experienced tripper and has taken such blotters a lot, so he knew what kind of dose to expect. He never had a blotter tested, but a reliable source told him they should contain about 160 micrograms a piece on average. Swim thinks this might be correct.
The trip
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Swim took the acid around 17:30. The acid kicked in rather fast, after 20-30 minutes swim felt that 'something' was starting. After about 45 minutes the open eye visuals started. Swim was stil reading something online at that point and the words started moving slowly and everything started 'breathing'. He told me any tripper would know what that means.
During the upcomming swim had other things on his mind as the breakup with his ex, but once the first peak was reached, he was constantly thinking about it. After thinking about his ex-girlfriend for a while, swim was very, very sad and was in his bed, crying. Somewhere in the first peak swim went out for a walk, but quickly returned because he was to paranoid as he lives in a rather crowded street. When the first peak became less intense, he wasn't feeling that sad anymore and was analyzing why he felt this bad about the breakup.
Around 22:00, swim felt that he needed a walk to think about what he should do and he feels that he actually got very good insights that probably had taken much longer without this trip. Somewhere during this walk, swim had a very scary experience. A cop car passed and started it's siren (not sure about this word) about 20 meters before him. Then, the car accelerated and drove past him.
After the walk, swim was feeling a lot better and he was slowly returning to a more sober state. He actually cleaned his room after this walk. This is the first time the state of his room improved while tripping . At 0:40, swim went to an electro party (it's not really his type of music, but it was the best party close to home). At this point he was in a state where he was feeling rather sober, but you could still see he was tripping by looking at his eyes. Also, he was not in a state where he could have decent conversations yet, he told me. He had fun at the party and stayed up untill the early hours.
Swim did this three days ago and he is actually feeling much better as before since then.
Conclusion
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Although there is a very good reason why almost everyone would advice against this, swim feels that the trip really helped him. He would definitely advice against it to inexperienced trippers but feels that he can somehow advice this to the very experienced ones. Swim had no trip sitter or noone nearby that could come over. Swim also feels that the trip would not have been usefull with a trip sitter, but that it might be safe to have someone watching your back from a good distance.