I'm a Girl, does that Mean I can't Make the First Move?

tay.s
asks:
I'm an 18 year old girl and have dated plenty of people. But my family has always been the type that believes guys should pretty much do the pursuing. My mom always says, if a guy wants a girl, he will make it known and he will try to make it happen. If he doesn't, he's not the right guy for you. Because of this, I've always let the guys come to me. My problem is that sometimes I'm interested in a guy and I feel he's interested in me, but it's not always the best situation to engage in a conversation like that. Like today, I was at an event geared towards kids. I was with my son but my mom tagged along. There was a guy running a booth and I was interested and he was definitely flirting but it just wasn't good for a full out conversation. Every time we passed him, he said something to me, even engaged my son and made him laugh, but he never took it a step further and I was convinced he wasn't as interested as I thought and ended up leaving with just a "have a good one". Sometimes I wish I could slip my number or ask him out or something but I never do because of my upbringing. Consequently, I end up thinking about it the rest of the day and often come to the conclusion that he must not have been interested in me like I thought and it kind of bums me out. I'm just not sure what to do about it? Should I stick to the family philosophy or maybe step out my comfort zone and go for it a couple times? Is there any way to feel a little more confident or know a little more clearly whether or not he's really interested?
Sam W replies:

The tradition of "men pursue, women wait" is still culturally prevalent, and a lot of families (yours included) teach their children that men should be the ones doing the asking when it comes to romance.

This notion is problematic for a number of reasons. It reinforces not-so-great ideas about how women are objects to be pursued, rather than people with wants and desires that they can (and should) act upon. It puts a lot of pressure on men to be aggressive pursuers, sometimes even encouraging them to push past women's boundaries because they believe women say "no" when they really mean "yes." It can also lead to men resenting women as a group because they have it "easy" when it comes to dating because they just sit and wait, and never have to worry about being rejected (spoiler alert: women get rejected plenty.)

In addition to all that, there are the very practical issues that you're running up against. If you create a dynamic in which one person is not supposed to convey their interest directly, you make it harder for everyone to figure out what's going on. Plus, there's nothing inherent in being a guy that makes you able to pick up on whether or not someone is interested in you, so there's no guarantee that a guy will "just know" to ask someone out. Yes, there are physical and verbal cues that can signal that someone is comfortable with you, or flirting with you. But the only way to know for sure if someone is interested is to ask them, and the only way for them to know about your feelings is for you to tell them.

Explicitness can be hard to do at first, because it runs counter to so many of the assumptions we have about how romantic relationships form, and unlearning those assumptions can take time. There's this idea that you just know when someone is interested in you, and through subtle signals and signs, you can communicate your desires to each other. No awkwardness, no corny jokes or nervous giggles, just a smooth courtship.

It's an appealing image to be sure, but one with almost zero relation to reality. People aren't psychic, and behaviors that you think are signalling "hey, I totally dig you, ask me out" might go completely over the other person's head.

The upshot of all this is that yes, I do think you should break with family norms and ask out guys who you're interested in. Especially because you're finding that waiting for them to approach you is frustrating you and making you feel as though you're missing out on opportunities for dates.

In terms of what you can do to feel more confident about approaching someone, there are a few steps to take. The first is to accept that there is no dude hive-mind. Every guy you flirt with, or try to pick-up, is a unique person with distinct preferences. So there is not one set of special rules that will work with every guy. This runs counter to certain common strains of dating advice. Everything form "The Rules" to pick-up artist subculture trumpets the belief that if you follow certain steps and use certain techniques, you'll be able to land a date.

Yeah, no. People are not computers where hitting a certain set of keys triggers a specific response. That's what makes dating, or even looking for a date, daunting for some people.

One way to make things a bit less daunting is to accept that rejection will happen, but it's not the end of the world. Does it sting? Yep, it does, but that sting is what you have to risk in order to meet cool people. Some people you're interested in you won't be interested in you for any number of reasons. That's just the way that human preferences work. Or, some people may like you or think you're attractive, but they're not in the market for a date (they're married or in an exclusive relationship, they're taking a break from dating, etc). But, by that same token, there will be people who are interested in you. And the quickest, easiest way to tell one from the other? Is to ask them.

That's not to say you can't use body language and other cues to help you work out someone's interest level. Lots of eye contact, open body language, laughter, and active listening are signs that they're at least interested in what you have to say and are enjoying your company. If they initiate little moments of physical contact (touching your hand, leaning in, etc), that's a sign that they're comfortable around you and might like to touch you some more. But, again, none of those signs are an absolute guarantee that they'll reciprocate your interest.

So what can you do as an actual approach? Keep it casual, low pressure, and specific. "Hey, I've really enjoyed talking with you. Would you like to meet for coffee/ice cream/dinner this weekend?" It conveys that you'd like to keep getting to know the person you're talking to, and sets up a specific time for another meeting. It's a clear invitation that they can decline or accept, rather than a vague "hey...you wanna hang out sometime?" If they say yes, hooray, they're interested! If they can't make that day/time, but suggest an alternate time or activity, then they're probably interested. If they give an "umm, I'll have to check and see...maybe some other time" odds are that's a soft "no".

And if they say "no?" Then that's a no. Accept it graciously and move on.

Just a word about flirting with or asking out people who are at work: it's not a great strategy (and that goes for flirting with/asking out anyone in a position where they're in a professional context, like volunteering at an event). That's in part due to the fact that people who are at work, especially if their work involves selling things/getting people to sign up for something or contribute to a cause, are going to be exuding a friendly, chatty vibe with everyone. That vibe can easily be mistaken for romantic interest, especially if you're someone who doesn't have a lot of experience with flirting. Too, if you read it as flirting when it's really not, you can end up cornering someone who isn't interested in you, but who's afraid to tell you that directly for fear it will affect their work. So it's a good idea to avoid asking out people in situations where you're the customer and they're the worker.

A final point to keep in mind is that asking people out takes practice. Don't beat yourself up if it takes time for you to get the hang of it. You may have a slightly steeper learning curve due to your upbringing, but you're in no way behind the average person your age in terms of knowing how to ask for a date. No one is born knowing all the ins and outs of courtship, and it's a skill to be learned, just like riding a bike or knitting. The more you practice, the more confident you'll become, and the easier it will be. And the more cool people you'll get to meet. There's lots of folks out there who'd like to get to know you. All you have to do is ask.

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