romantic or no? PLEASE give advice.

Back story: my best friend since high school started seeing my brother about a year ago. Their relationship has always been a little rocky. She's now 21 weeks pregnant and they have been broken up for 6-8 weeks. 
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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.
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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!