romantic or no? PLEASE give advice!

.

My brother still cares about her and wants to be with her but is having a hard time getting through to her. (She is the type of person that needs constant/daily reminders that she is loved and cared about) her birthday is coming up in about a week so him and I thought that he could buy her a nice date night type outfit and wraps it along with a letter expressing his feelings and a letter asking her to go on a date with him with the specifics included. I would deliver the gift to her and have her open it privately. And if she decides to work things out she would meet my brother for dinner that night.

.

Thoughts on this? Obviously we know there's a chance she will shut him down. But I'm just wondering if anyone thinks this could be a good idea. Thanks! 

**

*

EDIT: obviously he asked for my help and advice. Hence why I said "him and I thought."