I must emphasize that there will not be a single answer to this as Greek thought will be divided into several modes of thought just as contemporary philosophy is. Further, philosophers such as Plato and Aristotle might tell you to focus on larger or more meraphysical ideas rather than earthly pleasures.

As such I would recommend looking at moral philosophy such as Stocism or Epicureanism, of which I align myself to the former. Of what I say comes from Epictetus' Enchiridion which served as a life guide and manual for the casual reader.

First and foremost, it starts with a reminder of your individual power, there are things within your control and things outside of your control. You can control your mind and body but that is all, as such if you place power in trying to obtain things that are not yours, then you yourself are giving power to others.

Remember that desire contains in it the profession (hope) of obtaining that which you desire; and the profession (hope) in aversion (turning from a thing) is that you will not fall into that which you attempt to avoid: and he who fails in his desire is unfortunate; and he who falls into that which he would avoid, is unhappy.

By desiring something that isn't yours, you place yourself in the power of others, causing you to become unhappy from not having that thing. "But destroy desire completely for the present. For if you desire anything which is not in our power, you must be unfortunate: but of the things in our power, and which it would be good to desire, nothing yet is before you."

Further Epictetus emphasizes on chapter five that men (humans in general) are not afraid of things but rather our opinion. Wishing to be "better with the ladies" comes not from wanting skill but fear of not being attractive or something wanted. As such Epictetus would tell you to shed your fear and embrace that you can control your mind and heart, so lust and want not for you fear yourself rather than want for something.

Finally, He would emphasize this from chapter eight:

Seek not that the things which happen should happen as you wish; but wish the things which happen to be as they are, and you will have a tranquil flow of life.

I'm a philosopher, not a historian, but I do have an expertise in ancient Greek philosophy, and I would like to respectfully disagree with u/DonaldFDraper's claim that Aristotle and Plato wouldn't be good sources of ancient dating advice. ;) I think on certain interpretations, Aristotelian virtue ethics would actually be an excellent source for modern dating advice. I will be taking the Nicomachean ethics as my source. Please note that contemporary virtue ethics looks different from the Aristotelian sort, in many ways, but this is ask historians, not ask philosophers, so I will read Aristotle as literature and not theory. Dating itself was never brought up in the Nicomachean Ethics, but I will argue that both the concept of eudaimonia and virtue as the mean between two excesses could help a contemporary person quite a bit in dating. There is SO MUCH in Aristotle that one could argue answers OP's questions. I'm seriously geeking out right now. Anyway, moving on.

Firstly, the main aim of ethics as Aristotle saw it is to reach a place of "eudaimonia". There's debate about the best way to translate it in order to capture what it's really supposed to mean in the grand scheme of his moral theory. Rosalind Hursthouse has an excellent discussion of this translation difficulty in the first chapter of her seminal book on Virtue Ethics. She's a leading Aristotle scholar, so I will take her translation, as its most widely in use. Eudaimonia can be taken to mean "flourishing", which is a vague concept, but this vagueness is quite compatible with virtue ethics for several reasons that are unimportant here. But what's important to get is this:what it means to flourish is to act according to one's function, and to do this well. The function of the human, for Aristotle, was reason. Rationality alone was in his view the only thing that separated us from other animals. As it is what makes us distinct, it must be the case that our purpose is to study rationality, and be rational creatures. To be consistently and effectively rational would lead a person to eudaimonia.

But what does it actually mean to fulfil one's function as a rational being? For Aristotle, it meant cultivating two things: practical wisdom and virtue. Practical wisdom for Aristotle basically comes out of two things: education, and experience. He writes in Book I of NE:

Now each man judges well the things he knows, and of these he is a good judge. And so the man who has been educated in a subject is a good judge of that subject, and the man who has received an all-round education is a good judge in general. Hence a young man is not a proper hearer of lectures on political science; for he is inexperienced in the actions that occur in life, but its discussions start from these and are about these; and, further, since he tends to follow his passions, his study will be vain and unprofitable, because the end aimed at is not knowledge but action. And it makes no difference whether he is young in years or youthful in character; the defect does not depend on time, but on his living, and pursuing each successive object, as passion directs. For to such persons, as to the incontinent, knowledge brings no profit; but to those who desire and act in accordance with a rational principle knowledge about such matters will be of great benefit.

Basically, he is here arguing that in order to be a wise person, you can't just know the theory of action, you actually have to go out and do things, experience them, and live. Notice too though, that what Aristotle means by education is essentially being tutored by someone older and wiser. Indeed, in an Aristotelian framework, one learns virtue by asking for advice from an older person in your community who has been through something similar, and then practising what they tell you!

How would this apply to dating? I imagine that Aristotle it would argue that the best way to learn how to date well is to talk to people who are in successful relationships, and take them seriously. He would likely also argue that one ought to go out and actuall date, and reflect upon both your own successes and failures.

One huge gap in my explanation is how his theory of virtue ethics and dispositions further fits in here. I deliberately left that out, because I think his discussion of practical wisdom, though inextricable from his view on virtue and dispositions, actually gives a pretty good starting point to what OP seemed to be asking.

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