So I've been dating my current boyfriend for just over 2 years now, and at first we got along great. Unfortunately, due to money being very tight about 4 or 5 months into our relationship, we ended up moving in together to help each other out financially. What a terrible mistake that was. One bumpy year and a half later, and now I'm currently miserable by dating him. I don't feel like I'm in love with him anymore, although I still care for him as a person. It was my intention to find a place or two where I'd be able to move to when the time came and break the news to him while on a non-refundable vacation we'd planned for next week (we made the reservations several months ago, before I was seriously considering leaving). I figured discussing our options in a relaxed, comfortable place would be best. But then today, after confiding with my mother about what I planned to do, she told me that he'd asked permission to propose to me on our vacation. Now I feel like an absolute pile of crap and don't know what to do. I know I'm not happy, but I absolutely don't want to hurt him any more than I have to. Adding the fact that he thinks we're ready to be engaged just breaks my heart even more. What should I do, and how should I handle this? I have a few decent friends, but nobody really that would be able to let me stay at their place should things go sour. I'm heartbroken and depressed, anxious and feel like a terrible person.
Most Helpful Guy
Another possibility is he knows things aren't well and he senses you want to leave so this is more a manipulation tactict to get you to stay. Don't go on that trip ask your mother if you can stay with her and get out asap1
Most Helpful Girl
It does sound like a catch-22. That if you go on the trip, you'll lead him on and he may propose. If you don't, you'll lose money and upset him by foiling potential plans to propose.
Ultimately, I think it's best to bail out. Money can be earned back. Just imagine how much shame in combination with heartbreak he'll feel if he not only gets broken up with you, but much less after he gets his proposal rejected. Calling things off, or at least voicing how you've been feeling as of late, would be the better option. Quick and (relatively) painless.1