Giving compliments on dates

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I have a question for you all. I have been seeing a therapist recently to try to work through some of my issues with dating and relationships. Her biggest piece of advice so far is to start complimenting my date's physical appearance in some way, such as saying "You really look beautiful tonight" or something. I just have a few questions:

1.) Guys, is this something that you usually do? Girls, do you want or expect to hear these sorts of things? What's a good balance between saying enough and not saying too much?
2.) What exactly should I say, and how should I say it? One of the things that prevents me the most is giving a compliment like that without context. For example, if somehow her eyes come up in the normal course of a conversation, I have no problem saying "You really have beautiful eyes". But, if we're talking about completely different things, I feel very awkward and uncomfortable switching gears to say something like that.
3.) How soon is "too soon" for these sorts of compliments?
4.) Any other advice?

If I like how a girl looks, I tell her. I might say something like: "It seems like you always have a plan when you dress; you certainly know how to coordinate your colors." Or: "your hair looks pretty tonight." Or: I see that you are into fine clothes: I really like your cashmere sweater."

I would hold off on "you have pretty eyes" and such things until she gives you a wink or something like that. Or she caresses your hand so you could hold it.

Of course, don't say "you look shapely in those jeans LOL"

Avoid saying how "young" a person looks.

I told a girl a couple of days ago that I'm bad with names--but that I'll remember hers because she is so pretty. She told me, jokingly, that I have to go see an optometrist.

Absolutely you should! Just use your best judgement on what complements to give, cue kraftiekortie's advice! Of course, they are best given when you mean them.

You could tell her that she has a pretty dress or other things of that nature when you first see her for your date. Don't be shy!

Though contextual compliments are smooth, compliments needn't be contextual, either. You could ask her in the middle of a conversation or during a pause thereof: "Hey, can I tell you something?" When she awaits your answer, you could then tell her something like "I think you're super cute!"

Me personally, I love complimenting girls, even if they're not my girlfriends (not that I ever had one...), because it makes me feel good as it makes them feel good.

as for the timing and amount, i do not have a lot of useful advise, but i can offer a bit regarding the type:
be specific! do not say "i like your shirt", say "i like how your shirt complements your hair"
don't say "nice makeup", say "your makeup really brings out your eyes"

by complementing a specific detail over the whole picture, you show that you are truly interested and have payed close attention, rather then simply going over a list of default compliments

You should do it if you want to. And you should do it when and how you want to.

I don't expect my date to compliment me, because some people like to compliment and others don't, so I'd want them to just be themselves. If it sounds like it is forced, it will probably make me feel a little uncomfortable, so I'd rather they didn't in that case.

I much prefer being complimented on my mind than my looks, so I enjoy it when a my date says things like "oh I like the way you see that" or something. But again, only if it comes out naturally, not if they said it just because they thought it would please me.

Genuine expressions of appreciation of the other person, those that spill forth spontaneously because you can't help it, are a million times better than just trying to say or do the "right thing".

I find they are best used as an icebreaker during awkward silence. It shows that you are attentive to the person.

I like to get compliments on my looks, but if it is too much then I get turned off. It's because then I get scared that he ONLY likes me for my looks.

I am female and have the same opinion as Cafeaulait. I would limit the compliment to one thing per meeting, any more and it feels fake. Also, never comment on a women's body or focus too much on her physical features. Comment on an article of clothing, a nice piece of jewelry, the way she did her hair, or you could tell her in general that she looks nice/pretty. Avoid big punchy words like stunning or beautiful when you aren't officially dating.

Is your therapist single? I think she craves for compliments on her looks.