Happy Valentine's day! of course, anyone would appreciate gifts, but receiving them in Bitcoin would be another thing to appreciate. hopefully in the future you learn not to gamble your coins. one thing to remember, there is no point in gambling when you can simply appreciate what you have and enjoy your life. gambling would only bring you regrets.
If you and your date are like minded, I think that gifting bitcoin will work but it is not a good first impression if that is your first date especially if you do not have the same interest with bitcoin, you will look like you are paying that person for their affection, in short it's like buying a whore. Too bad that OP lost a lot in gambling, we all have our reasons but we have to find a way to resolve our problem or should I say, find a reason to quit your gambling. @ImHash is right, there is no point in gambling, but there is also no point in not having fun, my advice is to play but know when to quit.