Over the years, I’ve spent a great deal of effort learning how to tactfully meet women and interact with them. I’ve joined groups, taken up interesting hobbies, and spent countless hours observing and studying how women communicate in order to interact with them effectively. In many ways, I’ve been successful, as I meet more women now than I ever have in the past. Additionally, the women I meet now are from a wide range of my interest areas rather than from a single pool. But there is a group of women in my life (perhaps the largest group) that I’ve never learned to approach – until now.
Servers, waitresses, cashiers, and other customer service women present a difficult problem in that their job not only encourages behavior that can be misinterpreted as genuine interest but also holds them in a ‘captive’ environment and keeps them from responding normally for fear of offending a customer. Additionally, many who are genuinely interested in a customer are taking a career risk if they reveal their interest without that customer’s clear consent that it’s welcome. And so thus far, I’ve not made any efforts to approach these women, even if I really wanted to, simply because I don’t know of a good way to do it without putting them in a difficult position.
Yet the fact remains that, as a single guy, I interact with servers far more than I interact with most other women, and I’ve met quite a few who seemed genuinely interested in getting to know me. And yes, I’m writing about this now because there is one of these young women who has really been going to great efforts to let me know she likes me. She’s a hard-working and beautiful young woman who is introverted and a bit of a nerd, so I know she’s really going out of her comfort zone to connect with me, and after deciding to give her a chance, I discovered that I’ve never learned how to approach a server like her.
After doing quite a bit of research, the consensus seems to be to just leave a server a short and to-the-point note with an invitation to coffee or dinner with a name and number. A note doesn’t interrupt her work, it isn’t creepy or looming, and it gives a clear message of intent. The problem is that I’ve always been seriously opposed to asking a girl to contact me first. I learned a long time ago how important it is to get a girl’s number rather than giving her mine in hopes that she’ll contact me. Extroverted girls might take that step, but since I’m always drawn to introverts and shy types, they won’t respond even if they’d like to. That being the case, I’ve always taken the lead role and made the initial contact instead.
Of course, that creates a serious problem with this note-based approach to asking out a server, especially an introverted or shy one. I don’t know the answer to this problem, which is why I’ve been closed to approaching this category of women for years. But I’ve decided I’m going to find a way to do it, even if only by trial and error, and I welcome any insight or ideas from my readers on this topic. I’m always up for learning something new, and this is a puzzle I’ve decided it’s time I solved.