America’s favorite pastime isn’t baseball, couponing, or line dancing; it’s the hunt. Yeah, I’m talking about men pursuing women. 

Really all over the world, the one thing that all men have in common -even more so than their collective hatred of taxes- is the yearning to pursue women. 

Ever since the US was just a bundle of discontented colonies, the flirting and pursuing of women was in full swing. Back in the 17th century, the few single men available would ask the permission of the parents of their romantic interest if they could come over, meet the family, and bundle up (which consisted of being tied up in a sack and sleeping in the family bed as the girl and suitor in question are divided by a wooden plank). 

Yet since those awkward days, the hunt has imbued men with numerous courting tactics. Bundling evolved into personal ads, which then morphed into meeting women in public places like bars and restaurants, followed by videocassette dating, online dating, and now dating apps like Tinder, Bumble, and Facebook Dating. 

Nowadays pursuing women isn’t as simple as riding a horse over to her parent’s house and asking permission to be bundled up in a sack for a night and sleeping in the family bed. Today men have a myriad of methods to choose from when it comes to courting their beloved. 

In this article, we’ll break down how to pursue a woman you’re interested in by taking an in-depth look at numerous ways men go about hunting for romantic partners. But before we begin, let’s examine the role of the “hunter.” 

As gender equality rises, the role of the romantic initiator is evening out. That being said, the onus still heavily rests on the (hopefully) broad shoulders of the male. Men must still accept the role of “hunter.” But accepting this role is just as important as not over-pursuing and adopting the role of the “stalker.”

During my 100 date experiment, there was one guy I dated that took his attempt to court me to a creepy level. In the wee hours of the morning when few other souls were on the street, he’d wait for me outside of the bar I worked in at the time. This wasn’t a one-off situation but rather morphed into a trend that culminated in me having security walk me to my car after every shift. This is a situation where being a hunter can unravel out of control into something that no woman deserves. Always respect the woman you date and never make a woman feel uncomfortable. This is the first persistence rule of the pursuit.

As I mentioned, the modern dating landscape offers ample ways to meet women. We’ll go ahead and explore in-depth ways men most commonly meet women in the 21st century. You’ll learn how to pursue a woman on a dating app, how to pursue a woman you met through friends, how to pursue a woman you work with, and how to pursue a woman you met on your own. 

She Must Know You’re Interested From The Start

There is no benefit to waiting. Waiting gives that other guy from her office or Tinder the chance to swoop in and steal the girl you never had. Don’t delay signaling your interest until the two of you have spent more time in a platonic setting. There are thousands of variables in this world that are always working against you. Take control of your romantic destiny by initiating interest early. But just how do you make your interest known? 

If you’re chatting it up on a dating app, that interest is automatically understood. The context signals your interest for her. Although disclosing your interest changes when you’re interacting outside of a screen. 

If you’ve met your romantic interest through friends you’ll have to walk a tightrope. No need to use Native American smoke signals to make your interest known, instead be discreet. If this is a person that floats within your friend circle, showing your cards too early could make things weird for the entire group. Instead, do some recon. Ask your friends if she’s single and if she’s into you. When it comes to asking her art, be tactful about it. Acknowledge that you don’t want to mess up the group dynamic but that you think she’s awesome and would like to hang out with her away from your friends. 

After meeting a stranger at a cafe, dog park, or concert, be direct. Briefly chat it up before asking for her number. Tell her that you enjoyed the brief conversation and don’t want this conversation to be your last. Be honest with her and tell her that you’d like to take her on a date this week for coffee or a drink (always keep the first date light). When it comes to a stranger don’t waste time beating around the bush.

If you get rejected by a stranger realize that you’re only being denied by someone you don’t even know. Are you really going to feel down if a stranger rejects your offer to get a drink after a 5-minute conversation? You’re not. Because you don’t know them and they don’t know you.

How to Pursue a Woman You Met on a Dating App

You’ve got to love modern dating. Sure young Americans are having less sex than ever before, but never before has dating been so accessible. From the comfort of our own bathrooms, men and women can enjoy bubble baths while swiping left and right for their next romance. What Americans get wrong about dating apps is that they treat them like games rather than viable tools to help find love. The point of a dating app isn’t to stack matches like trophies, but to transition from an online match into a match IRL. This is how to do it. 

After you’ve created an awesome online dating profile, the virtual courtship process begins. 

Now that you have a match, it’s time to shoot her a message. As a rule, never message “hey” or a variant. Hey is the equivalent of a Facebook poke, but worse. It doesn’t direct the conversation in any way or add value to the dialogue. Use her profile to inform your first message. If she likes dogs, don’t just say, “I like dogs too,” but “Did you know dogs can smell cancer?” The goal with a first message is to receive a response. “Hi” is infinitely less likely to warrant a response than a message that addresses her profile and took longer than a second to construct. Here’s an article on first message examples for guys that’ll help you further. 

During these initial messages keep the conversation humorous and pertinent to her profile. Don’t pen long messages about yourself, do ask questions, and do respond in a timely manner. Ideally, you can score her number just a few lines after having sent that initial message. 

After a few messages have been exchanged, steer the conversation towards a TDL. After having chatted for a few lines, broach a TDL. This little-known acronym should be connected to something she’s into whether it be craft beer, riding bikes, obscure coffee, etc. Say something like, “Have you ever been to Fort Funston?” It’s here that you’ll receive a yes or no answer. Regardless of the response start selling her about the park. Once she knows a bit more about the date spot, ask her out to a date at that very location at a specific time on an exact day. Being direct and asking her out on a concrete date means that she’ll have to give you an unequivocal yes or no answer. 

How To Pursue A Woman You Meet Through Friends

An online match is private. An application gives you an intimate space that’s designated for the two parties involved. This is the antithesis of meeting a woman through friends. How to pursue a woman through friends requires a different tactic. If online dating is direct, pursuing your best friend’s friend isn’t. 

Imagine snagging brunch with a couple of friends. A woman your female friend brings along catches your eye and happens to sit next to you -how fortuitous. Show your interest by getting to know her. Ask how she knows the group and bond over a pair of jokes. Don’t worry if you’re not on your A-game, bottomless mimosas can be quite the wingman. 

Ask her questions, make eye contact, and after some dialogue call her out by her name. If the vibe is right even initiate touching, but remember, this is a brunch being attended by friends, keep the touches light and innocuous. You don’t need to turn your romantic aspirations into a spectacle. 

But Be Careful

It may be wise to not turn the heat up too quickly on your budding courtship. Doing so could burn the platonic bridges you and her have so delicately cultivated over the years with friends in your social circle. Learn from friends what her status is. Is she dating someone else in the group, newly single -what’s her deal? If you happen to learn all this before the hypothetical brunch ends, pull her over to the side and ask for her number. Only do this if you’re sure that she’ll give it to you. If you think it’s too early, trust your gut. Just don’t be afraid to ask because your fear of rejection. 

Once her number is in possession, ask her out using a TDL. If the date is set to take place three days after having asked her out, be mindful of not suffocating whatever spark you’ve got lit. Suffocation looks like meaningless text messages. Don’t ask her to type out her whole life story via text. Keep your questions tucked behind your tongue and wait to ask them in person.

The day before the date takes place, shoot her a text. Something like, “I’m looking forward to our date at Mountain Tam, see you at 11.” Always assume every woman wants to date you. She wants to win your affections, let her feel as though you’re super valuable by assuming her interest.  

The last point to keep in mind is your role as the hunter. Tone down your directness while hunting the friend of a friend. Employ tact, stay humble, and never make her feel uncomfortable. If asking for her number in person, make your intentions known. Also let it be clear that you can handle rejection with grace. Don’t be the dick that creates a divide in the social circle because you had to go and ask out a friend of the group. 

How to Pursue a Woman You Meet on Your Own

Fact, women are everywhere. There are no restrictions when it comes to meeting women. No one place is off-limits (except maybe a funeral). No matter where you are, seeds can be planted, and the fruits of your labor may grow. 

Let’s speed the chain of events up a bit shall we? You’ve just scored her number and have already asked her out. How you met her and how much time was spent with her slightly changes what happens next, but generally, the next step is uniform. 

After having met her, shoot a text a couple hours later. Simply message saying how it was nice to meet her and that you’re looking forward to your date in a few days. If you haven’t already secured a date, now is the time to ask her. If she doesn’t respond to your text within 24 hours you can start to doubt if she’ll ever respond. Wait a few days before reaching out again. The day prior to your date, feel free to pick up the phone and call her. If she’s young and you think a call is too aggressive, leave her a voice message. 

How to Pursue A Woman You Work With

Remember that hunter persona we’ve been conjuring? Tame it. Being overly sexually aggressive in a place of work is not only likely to lead to rejection but can result in termination as well. 

Generally speaking, I advise my clients to stay away from dating co-workers. If you MegaDate you shouldn’t have trouble finding a woman that pleases your romantic palate. Normally if a woman rejects a man, they both can move on with their lives without major consequences. But trying to strike up romance within the confines of the office is a risky business. 

Many SF companies actually have strict office dating policies. Companies like Airbnb employ the one-ask rule, meaning that you can only ask a co-worker out one time. Should she reject you just once, you’re no longer permitted to ask them out. And this is one of the more lenient dating policies around the Bay Area. 

Despite the risks involved it’s only natural that you’d fall for a co-worker. You two spend a copious amount of time together, you constantly chat, face challenges, achieve milestones, etc. It makes sense that you have the hots for your desk-mate. So what do you do?

My advice is to play it cool and let her pursue you. Sit back, be yourself and let her reveal her feelings for you. Wait for her to reveal her cards by asking you if you’re seeing anyone else. Should she begin to make inquiries into your romantic life, that’s a signal that she’s into you. 

When you ask her out, don’t do so on a company platform. Don’t use Slack or a company email to ask her to get a drink. Don’t use any stream of communication that your company can use to track you. Considering you see her every day it’d be chicken of you to ask her out via text. Instead, one day after work has finished, walk her to her car and pop the question. Make sure you two are private, use tact, and don’t put pressure on her. 

In Conclusion

Surely while reading this article you’ve gone through a mental list of all the women you want to ask out. What you just read is nothing more than a primer on how to pursue a woman you’re interested in. You may feel as though you need a bit more information before you go all Don Juan on the local dating scene -if that’s you, no worries, I’ve got you covered. To become a dating maven, start by booking a 1-on-1 Skype session with yours truly. In it, I’ll outline how we’ll turn you into a major player in the dating scene. We’ll also determine if my 3 month coaching program could help you reach your goals even faster.