Most Helpful Guy
I agree with another opinion on here. You don't want to be TALLER than your date if this is the first one. Some guys are uncomfortable with a taller woman (because they don't realize how great tall women are)... and it may be something that the guy doesn't have a problem with overall... you just don't want to intimidate him when you first meet. First impressions are everything.
Other than the first-date scenario you've presented, I think there's nothing wrong with your height in or out of heels. I'm sure with 4" heels you are sexy as hell, and don't let anyone tell you differently. Anyone who doesn't like it... well... you can look down at them and tell them to get lost. Better yet, don't even worry about it. Guy that care are too insecure about their manhood, and you don't want that. Girls who care are just jealous of your height, and you don't give two shits.
You are you, and you were made perfectly... so rock those heels, stand up straight, and be proud of your tall beauty.
Except on this first date :-)
Most Helpful Girl
I'm 5-8 I wear heels anytime I damn well please! Haha honestly I used to be concerned that I'd be too tall, but then I just kinda stopped giving a shit. There are people that are gonna think you're too tall even if you are 5-6. It's due to insecurity or predilection on their own part, it's nothing to do with you. Some guys are gonna find it hot, some guys will feel emasculated. But do you want a guy who feels emasculated by the mere fact of you being tall? I wouldn't want to be with a man who's identity is seemingly wrapped solely around the differences in our height.
Go on the date in your heels, if the guy you're out with is out off because you're in heels, leave. Fuck him, wear your heels, feel beautiful, there are tons of guys who would love to be out on that date and I'm pretty sure you'll have some staring at you that night.
Like I said I'm 5-8 I wear heels that make me up to 6-1, my fiancee is 5-11 or 6 (if he's in dress shoes) he doesn't care. Even if I'm taller than him. I wore heels on our first date and was an inch taller, I asked him about it and his response was "why should I care, your height has nothing to do with me, you being tall doesn't make me any less of a man. It just means I'm the lucky guy with the tall girl"