Why is Valentine's so hard?

Almost 2 years ago, I was with my ex and had a valentines weekend together as we were long distance... the long n short of it was it was an awful time, involving food poisoning and the lack of knowing the word no and that was the last time I saw him in person before he dumped me...

After last year on my own, I've started dating someone else and he means a lot to me... he is one of my best friends and I knew him while dating his ex who wasn't great to him...

I want to do something for him for valentines days but a) I dont know what type of effort to put in as I'm not great with the holiday, b) I dont want to over do it as he can't effort to do a lot or under do it as I want it to be special and c) I keep thinking back to that bad weekend that I now have associated with valentines day..

Does anyone have advise on how to approach asking him what type of effort he wants put in valantine day without putting pressure on him or making it sound like I'm not interested?
1 mo
I'm getting the overall impression that I'm over thinking this (which for me happens a lot in all honesty)... I'll think of something small and simple, thank you :)
Why is Valentine's so hard?
Add Opinion