Always Chat Up Salesgirls
Every man who aspires to be a Don Juan should make it a point to always — always! — make light conversation with female salespeople, cashiers, "baristas", and other retail service workers.
For one thing, chatting up salesgirls and cashiers helps to create the habit of talking to women, which leads to learning more about women and becoming more comfortable in their presence.
The fact that the particular cashier may be half your age and, demographically speaking, have little in common with you is irrelevant. She is a woman. She may be a unique human being in a million different ways, but fundamentally she thinks likes a woman and reacts like a woman. You can learn a lot from her.
Secondly, your conversational efforts will usually be appreciated and will make you a more memorable customer.
This is particularly useful in places like coffee or sandwich shops, juice bars, newsstands, convenience stores, or anywhere else that you are likely to become a "regular".
What you want is to become the kind of customer whose arrival immediately brings smiles to the workers' faces. Before long, THEY will initiate the conversation. In addition, other customers pick up on the fact that the staff likes you; you become, in effect, "validated".
Your attitude should not be that you're trying to pick up the salesgirl, but to simply acknowledge her in a way that is friendly and appropriate. Over time, you may well develop a romantic relationship with her, or with someone she wants you to meet, but that's not your immediate objective.
Let Me Give You Some Real-Life Examples
Several times a week, I go to a locally-owned coffee shop that makes some of the best espresso I have ever had. In fact, it's so good, I drive past two Starbuck's to get there.
My second or third time there, I said to the barista (young, female): "I'd like one of your famous double espressos". She looked at me with a little smile and said, "Are we really so famous?" "Well, if you're not, you should be. Your espresso is way better than Starbuck's."
The next day, the barista greeted me with, "Back for another 'famous' double espresso?" After that, we usually exchanged a little chit-chat each time.
As I became more of a regular, one barista would introduce me to another, and before long I had a friendly relationship with the whole crew. Once a certain familiarity was established, it seemed normal and appropriate to make personal comments and give compliments ("Hey, I like your new haircut, Julie. It looks great short!").
Although I have never dated any of the baristas, my relationship with them indirectly led to a romance with another customer.
I was asking Julie one day what had happened to Francine, a barista who had seemingly disappeared overnight. "Oh, she got some bad news from her parents back in Michigan. Her father had a stroke two weeks ago, and Francine felt she had to go home and help out."
We commiserated a bit about Francine's plight, and then I sat down to drink my espresso and read the paper.
Almost immediately, a good-looking woman at an adjacent table said, "Excuse me, but were you talking about that young woman with the long black hair? I was wondering about her, too — I always liked it when she waited on me."
We kept talking (you should ALWAYS keep the conversation going, if you're interested in the woman), and a few minutes later we were sitting at the same table, and the next night I was enjoying a wonderful dinner at her house.
The point is that frequent interaction with women — no matter how superficial — is a good thing. You never know where it may lead, and at the very least it keeps you in practice and boosts your self-confidence.
(Note: I reluctantly exclude waitresses and bartenders from this list, because a) they are usually so busy that even friendly small talk is annoying to them, and b) they are hit on so often that they have developed an immunity to anything resembling an advance.)