How Do I Approach Women Without Making it Weird?

Hi Dr. NerdLove,

First of all, thanks a lot for all the content that put out there. It’s really a treasure to have a person like you on the web when majority of dating advice on the Internet is just a single step away from turning into something worse and manipulative. 

Now to the question, a bit about myself – I’m 22 (almost 23) years old and I’ve been trying to work on myself, getting my life in order, quitting bad habits, and taking up the courage to be more social. I only came to realization, recently, that I fall under the spectrum of this anxious attachment thing, and I’ve been trying to get a hold of it, trying to give people some space. I realize I’m doing exactly opposite  with the questions like “how do I approach women”, right, as if I looking at them like a monolith and somehow they needed to be approached differently than the random men that I come around the day. And I really don’t, it’s that with men, they’ll usually be doing something related and I can play on that to ask “what’s that thing”, and to the next, “it’s bit cloudy or sunny”, then to next “so how was your day”, and so on. With women, even with similar situation, I’ve seen them giving side eyes, “mean look”, or straight up ignoring. At some level, I understand why they do that, guys trying to pick them up, hit on them. Not that my question doesn’t eventually land up in the same category, but it’d be just awesome to get to know people in general but especially women as I don’t have many female friends besides classmates and general acquaintances, say neighbor or something. Basically I want to get to know people.

So the thing is, everyday I have to drop my younger brother to his coaching class in the evening and as the place is bit far, going back and fro to home is not a good idea. So, I decided I’ll drop him off to his class and spend sometime in a park nearby. Now I sit around, with earphones plugged to my ears, music on. Sometimes, I sit idly, waiting and observing things in the park, and obviously, people as well. I see people I want to talk to, they’d be random men, women. It’s easier when they’re holding or wearing something unique or eye catching and you’re actually curious about it, but how about when there’s just nothing you can catch your eyes on but you still want to talk? Can’t be like, “you are cute”, I’m straight but I should try that to get some ball rolling with men as well, then can I be comfortable saying it to women, but also to ones who sometimes I may actually be attracted to? I don’t know, I’ll make it weird for everyone, or be that weirdo in the park that people will gossip about, God help me.

But honestly, how do I “approach” approaching the right way, keeping in mind, the social context? But I don’t know how should I pick it better. What do you do when they’re in a group or just with a friend talking? It’d be rude to approach them then, I’d be surely ruining their good chit-chat, hey what’s this rando doing here?

Just framing it as “approaching women” sort of question instead of “how do you approach women but also, people in general”, this framing somehow feels like I see women as something other than “people”, or I don’t know any better way to frame it. Meanwhile, it’ll draw more men looking for the same to better answer from you who may just not be as receptive to basic gender neutral social norm. But who am I lying to, I’m looking for some love and connection, and this should not be the way I find that. How about going back to meeting and getting to know, and date people through a mutual friend, that’s it. I need to widen my friend circle. Help, I’m out of words.
 
Looking For Groups

You’re overthinking things, LFG, and honestly, it’s starting with framing this as “approaching”.

So, I know I refer to doing approaches or talk about “cold approaches” and “warm approaches”, so I’m contributing to the issue. Gonna put that right out at the start. But part of what trips people up is when they refer to “approaches” as some sort of separate form of interaction versus… well, just starting a conversation with people. That’s literally all approaching someone is about: you’re trying to start a conversation with them. When we start to think about it as “doing approaches” rather than just talking to folks, we end up treating it as having different rules, guidelines and inherent behaviors. This, in turn, leads to folks drastically over-complicating things in their heads and ultimately psyching themselves out.

Especially when they’re thinking of this in terms of romance or dating.

But whether you’re trying to just be more social and make more friends, or you’re trying to find Ms. Right (or Ms. Right Now), the process is ultimately the same: it all starts with a conversation. Everything else – the opener, pivoting to another topic and so on – is in support of that conversation. These aren’t hard and fast rules so much as just a general structure to serve as a guide and best practices; they’re a way to help folks feel like they know what to do next and avoid common pitfalls. However, the more you develop your social skills, the less you need to rely on the structure. It’s like jazz: once you understand the basics and the “rules”, you’re better able to improvise, vamp and go “off script” as it were.

Now with that in mind, let’s talk about some structure that you can use to grind out your social experience points and get more comfortable just being a cool guy that folks like to talk to. First and foremost: like most folks, you’re sweating the opener and looking for a plausible excuse to go talk to someone. Having an excuse, no matter how obviously flimsy, isn’t strictly necessary; most of the time, these can be akin to having training wheels on your bike. Things like the indirect or opinion openers – where you have a pretense to talk to someone, like asking their opinion about something – are handy for folks who feel nervous about talking to strangers. It’s less about “don’t let them know what you’re really doing” and more “here, this will make you feel more confident in getting the conversation started.” While having an excuse to talk to them can be helpful, it’s not an absolute necessity. “Hi,” is as perfectly good an opener as something like getting someone’s opinion about your friend’s jealous girlfriend.

In fact, in a space like a park – that is, places where people are social, but don’t explicitly go to in order to find dates – then you’re often better off just being low-key and friendly. That means taking things slower and gradually, rather than coming in with the same energy you might have trying to talk to someone at a bar. s

There are a lot of ways you can get a conversation going in those spaces. The indirect ways may be easiest for you at this moment. The most obvious would be to pay someone a compliment about something they’ve had an active hand in, like their clothes or their hairstyle. If, for example, I see someone wearing a shirt that references a property I recognize, I would say something along the lines of “hey, nice shirt, I love INSERT_$PROPERTY_HERE!”. In fact, I did this just the other day when I saw someone wearing some My Favorite Murder merchandise styled to look like a death metal band’s logo. It got the conversation rolling as we talked about the podcast for a few minutes, then we said our goodbyes and went our separate ways. Hell, depending on the property, I might make some reference, a nerd shibboleth, if you will. There was one time I was jogging on a local hike-and-bike loop when I passed someone in a Mass Effect hoodie. As we passed, I said “Shepard” in my best Wrex imitation. He responded with “Wrex…”. When we both passed each other on the other side of the loop, he did the same thing. “Wrex…” “Shepard”. If I hadn’t been more focused on getting my run in, it would’ve been a good time to stop and have a conversation.

Now, there isn’t always going to be something immediately obvious to comment on and that’s fine; most of the time you can just tailor how you start the conversation to your location. At a bookstore, I might (and have) ask someone for a recommendation. At a coffeeshop or sitting at the counter at a restaurant, you might just make a general observation out loud; these often serve as an informal invitation for others to comment and respond.

With a group, the key is to treat the group as a singular entity, rather than trying to address any one person. In those cases, having a reason to talk to them – “hey, can I ask about the game you were playing?” for example – is helpful. From there you can introduce yourself and get to know the folks in the group.

One thing to consider – especially if you’re going to spend time at the park waiting for your brother – is familiarity. If you’re a regular at some place, whether a bar or restaurant or a place like your local park, you’re likely going to see some people over and over again. The fact that you’re both regulars makes it much eaiser to just say “hi”. In fact, saying “You know, I see you all the time here and I realized I’ve never actually said hello…” is a great way to start a conversation.

Now, regardless of how you start the conversation, you want to pivot to actually getting to know them. In a public space like the park, the most obvious pivot is an introduction. A simple “my name is…” is all you need. From there, you can shift to being more direct about getting to know them – “so, what brings you out here on a fine day like today?” – or sharing a little about yourself first: “My brother takes a class around here; I love how peaceful/energetic/social/whatever the park is…” In both cases, these are bids for commonalities; you’re seeing what, if anything, you have in common with them. After all, we instinctively like people who are like us. Finding those moments where you or they can say “yeah, me too!” or “I know, right?” help solidify a connection, turning a stranger into an acquaintance.

A thing you might want to keep in mind is that as much as you want to approach others, you want to be approachable as well. Making sure you’re not giving “do not disturb” signals like having headphones on, having open and friendly body language and making sure you have a smile or positive expression helps send the signal that you’re friendly. Things like scowling (or having resting murder face), closed off body language or focusing exclusively on your phone or  your book or what-have-you tell people that you’re not interested in talking to others. It’s also good to be dressed well too; you don’t need to be dressed to the nines, but you also don’t want to wear the stained and ragged sweats you might wear while doing yardwork or cleaning your kitchen. The more your presentation is on point, the more likely folks are going to want to engage with you, whether you initiate or they do.

This also goes a long way towards not being an accidental creeper. If you’re keeping things low key, friendly and platonic, you’re not likely to creep folks out. While yes, women will have their guard up if they think you’re trying to pick them up, if you’re talking to them the way you’d talk to another man, it’ll be clear that you’re just being social. And if you’re just being social, instead of actively hitting on woman after woman, then you’re not likely to be gossiped about… or, rather, if folks talk about you, it’ll just be in the sense of “oh, I saw LFG at the park the other day”.

A final thing to keep in mind is that – especially if you’re dealing with regulars – is that short and sweet interactions can be better in the long run than having a prolonged conversation where you try to speedrun the process of “stranger-to-friend”. A series of short conversations where you leave on a positive emotional note is better than trying to ride that particular interaction like Slim Pickens until it hits the ground. “Always leave them wanting more,” is as valuable to meeting folks as it is to showbiz. It’s easy enough to say “hey, I have to go pick up my little brother; maybe I’ll see you around next time,” and take your leave. That makes it that much simpler and more natural to pick things up next time you see them.

Incidentally, being social and friendly makes it much easier to pivot to getting a date. If you’ve had a few good conversations with someone and you feel like you’re catching a vibe, nobody would be scandalized if you were to ask them if they would like to get a cup of coffee. They might still say “no”, but it will feel organic and a natural evolution of your interaction with them, instead of making you seem like you’re cruising the park for dates.

Good luck.