Yes. Especially if success is partly defined by "not wasting money on other people". But even if it isn't. You have to be humorous about it but, yeah, the only time I would ever buy a woman I just met a drink is if it is her birthday. I'll also buy second rounds if the girl buys the first.
On the other hand this tradition makes going out to bars with my girlfriend a lot cheaper since she can just walk away for a minute and someone will come up to her and buy her a drink. After which she comes back to me, drink in hand. (ETA: Though, I don't think she's ever asked for a drink. She's much too nice for that. People just come up and offer.)
As a non-drinker, I often passed proffered drinks onto my friends, who could make use of them. Obviously I would never ask for a drink, except maybe a glass of water.
Followup to: Do you have High-Functioning Asperger's Syndrome?
LW reader Madbadger uses the metaphor of a GPU and a CPU in a desktop system to think about people with Asperger's Syndrome: general intelligence is like a CPU, being universal but only mediocre at any particular task, whereas the "social coprocessor" brainware in a Neurotypical brain is like a GPU: highly specialized but great at what it does. Neurotypical people are like computers with measly Pentium IV processors, but expensive Radeon HD 4890 GPUs. A High-functioning AS person is an Intel Core i7 Extreme Edition - with on-board graphics!
This analogy also covers the spectrum view of social/empathic abilities, you can think about having a weaker social coprocessor than average if you have some of the tendencies of AS but not others. You can even think of your score on the AQ Test as being like the Tom's Hardware Rating of your Coprocessor. (Lower numbers are better!).
If you lack that powerful social coprocessor, what can you do? Well, you'll have to run your social interactions "in software", i.e. explicitly reason through the complex human social game that most people play without ever really understanding. There are several tricks that a High-functioning AS person can use in this situation: