Downtown San Francisco during the work week is always swarming with millennials in clothing styles meant to convey ‘simple, smart and purposeful’ yet for many, dating life is proving to be anything but that. The millennial clients that I coach through professional and personal life goals came of age in a time when digital technology had already changed how people communicate, disrupting social rules of dating among other mainstays of modern society. Thirty-nine percent of Millennials admit to interacting more with their phones than the actual people in their lives, making them even less likely to to talk to strangers without clear cause in their everyday comings and goings. Many millennial men who’ve achieved professional success are now ready to marry, but are realizing the strategies they used to find casual sex partners aren’t cutting it for finding ‘the one‘. With no time to sift through dating profiles or spend nights in bars, these guys are engaging coaching to develop proactive dating strategies that set them up for success in their daily activities.
“I want to meet a really smart woman, much smarter than me! Someone who is passionate about pursuing her goals, driven by values that we both share. I want to be attracted to her mind more than anything! But she should want to be healthy and fit and enjoy being sexually active for us to be truly compatible. Financial independence is important too, since living here is so expensive. Is that too much to ask?”
That’s Silicon Valley in a nutshell, and honestly that’s not even a tall order compared to what my high-achieving female clients have on their marital check-list. So while online dating has been effective for solving most people’s casual sex needs, it feels agonizingly inefficient to most people ready to meet someone marriage-worthy, especially with personal brand consciousness and FOMO influencing millennials’ major life decision-making process. I encourage my single clients to attend curated social events or engage in recreational activities with a male/female ratio that benefits them, increasing the odds they meet people of similar caliber who share mutual interests. I ask them to take the approach“if I had to solve this problem in the next two weeks, how would I do it? What can I do to get started today?” which gives people a sense of urgency and gets them ready to apply practical solutions in the here and now.
After mapping out a few actionable plans with a male client, he earnestly asked “is it ever ok to just approach a woman in public these days? You know without coming across as desperate or creepy.” Admittedly I was taken aback by this question – I was struck by the difficult task of overcoming social anxiety they’ve spent less time addressing thanks to technology, while leveraging enough social finesse to engage others in a respectful and compelling way. Many millennial aged men understandably prefer to play it safe in unclear circumstances, or risk coming across like a cheesy pick-up artist (PUA). Have millennials come to rely exclusively on dating apps, social introductions, singles bars and events that serve the function of bars to form romantic connections? Has the heterosexual male to female ‘cold call’ approach become totally obsolete? Like the evolutionary equivalent of the human appendix, wisdom teeth or tonsils, once useful in our dark past but at best should remain dormant or at worst may trigger pain and suffering? 
Once upon a time men were far more likely to approach women in public outside of well-defined social circumstances, when our society was more deeply rooted in the notion that ‘masculine persistence wins the heart.’ American media largely produced by men has been dominated by storylines that convey if a woman responds to a man’s advances with disinterest, she can be persuaded to change her mind through a combination of charm, wit, and low-key psychological warfare. This dynamic calls for female passivity, contributing to how women are treated as ‘fair game for romantic pursuits’ in public spaces. The time of reckoning for gender inequality has come with the #metoo movement, an activist-led eruption of female empowerment that has become a global phenomenon, upending the longstanding tolerance of objectification and abuse of women for the purpose of male sexual gratification. Though gender equality across all realms has a long way to go, it is still possible for men to safely and respectfully engage women in public by learning to read social cues with greater sensitivity. It will likely not be easy or feel comfortable. As I said to my male client “approaching a woman in public is graduate-school level game– we’re working on social skill mastery at the kindergarten level- first things first.” (My clients are sturdy and know I don’t dish out what I know they can’t take!)
If you want to approach a woman in public but are unsure of how to proceed, take the time to read the situation closely. This may take time you don’t want to spare- but keep in mind, a rushed approach increases the chance of a failed mission.
HOW TO’S:
- Make sure this woman is not wearing a wedding ring. This is an easily avoidable rookie mistake! Practice discreetly checking out left hands in various situations so you can be ready to quickly assess when it matters.
- Respect women’s time. Does it look like the woman is in a perceptible hurry? Is she engaged in an activity that she’d probably prefer not to have interrupted? If she’s busy working on a laptop she probably won’t welcome small talk- wait until it’s obvious she’s taking a break to speak to her. Is the woman clearly relaxing, enjoying a meal by herself or having some personal downtime? If she responds with only a fleeting or absent smile, minimal verbal response or eye contact, take the hint and keep it moving. Persistence in the face of a minimal response is only going to feel uncomfortable and annoying to her.
- Pay attention to eye contact. Has the woman made purposeful, positive eye contact with you at least a few times? Catching a woman’s eye once might be accidental, twice might be her checking to see if you are still looking at her. Women naturally check their surroundings for their own safety, and women find they need to keep an eye out for guys who might be staring, stalker style. Your job is to make sure you come across as friendly and safe– if you’re so nervous you can’t smile in the split second you catch a woman’s eye, you might not be ready to approach a woman in this manner. Practice talking to women you don’t know in social settings where people are clearly expected to mingle so you develop a sense of how to accurately read non-verbal cues.
- Drop the idea that channeling alpha male confidence will lead to a positive outcome. Guys are really attached to the idea that exuding cool confidence is what women want. It’s refreshing and much more likable if you can manage to be yourself and talk with a woman like she’s a person not an object to win over. Better to be awkward and able to laugh at yourself if the situation calls for it! Take it from a woman- we’re often just as concerned with first impressions, and you’ll make it much easier for her to respond to you if open with something genuine and friendly.
- Ask her opinion about something related to the shared situation you’re both in, and be sure to listen and show appreciation for her response. This is simple enough to do, especially if she’s in nearby proximity. Respond with something of equal tone, and if possible include an opportunity for her to keep the conversation going.
- Get out of your comfort zone, and use light-hearted humor to break the ice. Authentic self-deprecation and self-declared inexperience is an easy way to gain a moment of sympathy from women. Women are natural care-takers, teachers and experts in many, many things! Guys, if you put yourself in a situation where there are women who are excellent at something, you will stand out not only because you’re willing to risk looking foolish, but also because you’re interested in something they clearly enjoy. This only works if you demonstrate a genuine interest in learning. If you keep at it long enough, women will likely take pity on you and offer some support. I’ve seen it happen a million times before!
Adopting these strategies aren’t meant to guarantee that you’ll get a date after perfecting them, but can work to start an engaging conversation that could potentially reveal a reason to stay in touch with a woman as result. Good luck out there, and you’re welcome!
A 30 year old male client of mine shared with me how 
Deep Mindset Coaching, LLC 
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