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If it's still not working, it should be a bug. You can send the bug report to us by following the steps here: https://steamcommunity.com/app/1084600/discussions/0/3713810544748132640/
Edit to add: I mailed my save file.
Exactly the same issue I had.. it never resolved itself. I restarted my save because it was the same every day for a couple of seasons. I had Logan maxed out as soulmate and I had Andy as a BFF... so I just started again to see if it happens again. (Also never once chose a flirt with anyone else). It seems some have no problem and the rest of us can't marry him. So sad.
I had previously chosen 1 flirt option with Owen (when his friend came to town) and 1 with Ernest (the bit with Banjo and the wadded up piece of paper). I had also told Unsuur "Let's be best friends."
I also made it a point to befriend Andy, but that's because I genuinely like the kid and wanted to adopt him no matter what happened with Logan.
I flirted at every opportunity after the first one, kept giving him gifts even after the relationship was maxed, and he confessed to me. We had a hot date. I kept asking him on dates and giving him gifts.
I already had the engagement ring from a while back because I like being prepared. I asked him on another date, took him to the proposal place, and got the option to propose (E). I did and he said he thought I'd never ask or something to that effect. Then we were considered married and he moved in (sleeping with his hat on lol), but I did have a wedding ceremony at the church on the following Saturday. Got to the church, put on my pretty dress, took a couple of pictures, clicked the book on Miguel's desk, and the ceremony started.
The wedding picture the game took is goofy because Logan is barely in it lol but the whole thing worked as intended. I did not throw a party because I didn't even think about it.
I should have said that this was a game I had been playing for quite a while. I am now replaying the game from start to see if I can duplicate the success. I have no idea why it worked for me and some people, but doesn't work for others. I have no idea if anything I did was different than anybody else.
I will try to keep up with both threads to offer anything else I notice, but it will be a while. We just got the bridge finished in my new game and I have a lot going on this week so I don't know how much time I'll have. Darn you real life!
I chose every single flirt line that popped up with him.. even the ones made me laugh so darn much.. talk about awkward.. so unfortunately, in my case, that did not help. I still couldn't. Here's hoping it works this time because I really don't feel like marrying off the poor girl to someone else.
I started a new one as well to see if there's something I missed in the points, but I will take a lil to get to Logan. Was also only going to take Andy to Good friends (or whatever the title is) to see if it bugs out or there was something I missed not posting in the list of things done.
I mean, my main is over or at 2 years old so it's not a new play through or it hasn't been through however many patches. Would think if anyone had a problem, she would of. Was wrong though. :/
Just for you'all information!
IT WORKS!
So here is another data point for y'all. I am also friends level with Andy.