Welcome back to our summary of “Dating Sucks But You Don't“ by Connell Barrett. You’ve made it to part 3 so give yourself a much deserved pat on the back. Now that we've explored the nuances of effective communication, physical escalation, and leading your dates on an unforgettable journey in the previous second part of our summary, it's time to dive deeper into the art of approaching women and leveraging advanced dating tactics. Building on the foundational principles and mindset shifts covered earlier, this next section will equip you with the tools and strategies necessary to confidently initiate conversations, overcome approach anxiety, and take your dating game to the next level. Whether you're looking to get a woman's number in 60 seconds, explore the possibility of a ménage à trois, or simply charm a beautiful stranger, Barrett provides a wealth of insightful and actionable advice to help you navigate the modern dating landscape with poise and authenticity. So let's dive in and uncover the final pieces of the puzzle that will empower you to find the “Right Person, Right Time“ for a truly fulfilling, long-term relationship.
Approaching Women
Many single men find it tough to walk up to a woman they are interested in and strike up a conversation, whether it be at a bookstore, a coffee shop or on the street. Since attractive women often get bombarded with attention from guys, by being able to confidently approach them, you can set yourself apart from the competition. Barrett highlights the importance of being able to express one's authentic self in order to attract women. Confidence and vulnerability are seen as attractive qualities that women appreciate, and Barrett believes that mastering the art of approaching women is something that can be honed with time. By learning and practicing approach techniques, men can increase their chances of getting phone numbers and dates.
Obstacles to Approaching Women
When it comes to approaching attractive women, Barrett says there are three types of single men - the 95% who avoid approaching, the 4% who approach with a painful win-lose mindset, and the "1 Percent Men" who use a win-win blueprint.
Approach Anxiety and Fear of Rejection
The dread of rejection is often the main catalyst for approach anxiety, a state of nervousness or hesitation that deters men from initiating conversations or flirting with women they find attractive.
Many men perceive rejection as a potential source of pain encompassing feelings such as embarrassment, shame, anger, frustration, disappointment and a sense of inadequacy. Men will often catastrophize and make rejection seem larger than life, triggering a “fight-or-flight” response that makes them want to avoid approaching. Interestingly, research suggests that the discomfort caused by rejection may activate brain areas associated with physical pain—a remnant from times when social exclusion posed a lethal threat.
Win-Lose Mindset
Barrett says a win-lose mindset when approaching women is a major problem that leads to painful rejection and avoidance behavior. A lot of men see interactions with women as either winning or losing. If she is interested, they consider it a victory and feel validation. However, if she turns them down, it feels like a personal failure and a blow to their self-esteem. This mindset turns an approach into a high-pressure scenario where one's sense of self is at risk. This imagined "judgment" on one's worth intensifies the level of fear and magnifies the agony of rejection.
How to Overcome the Obstacles to Approaching Women: The Win-Win Blueprint
The Win-Win Blueprint refers to adopting a mindset where every approach to a woman is seen as a success, regardless of her specific reaction. Here’s a detailed analysis and actionable steps on how to effectively use this blueprint:
What is the Win-Win Blueprint?
The Win-Win Blueprint is a paradigm shift from the typical win-lose mentality that most men have when approaching women. The Win-Win Blueprint redefines success by deciding that every interaction you initiate with a woman is a win because you either:
Get a date/number (win)
Grow as a person by taking action and building your confidence (win)
This mindset makes it impossible to truly “fail” because you’ve redefined success. Even if she’s not interested, you still succeed by building your character and becoming a man of action.
How to Effectively Use the Win-Win Blueprint
Link tons of pleasure to approaching, not pain Make a list of all the positive outcomes linked to approaching - potential dates, confidence, growth, expressing your true self, etc. Then minimize any associations with pain or negative outcomes from her not being interested.
Realize rejection isn’t that bad The approach anxiety beforehand is often worse than the actual rejection, which allows you to think “Hey, I'm still alive, that wasn’t too bad, so what was I afraid of?”
Redefine rejection as a “win” View any rejection as a win because you took action, built experience, and are one step closer to meeting someone you click with. She can’t truly reject you as a person since she doesn’t know you well.
Assume attraction when approaching Walk up expecting and believing she will be interested in you. This positive mindset can become a self-fulfilling prophecy where your confidence attracts her.
Use empowering language Describe approaches that don’t lead anywhere as “blowouts” rather than “rejections.” A blowout is funny and takes away the sting. Say “That approach was awesome!” after each one.
Follow the “Rule of One in Three” Expect that about one out of three women will be interested when you approach authentically. Embrace that the other two won’t be interested as part of the process. Accepting that not everyone will reciprocate interest paves the way for genuine connections without undue pressure.
Take action, don’t just consume content For every hour spent learning dating advice, spend an hour approaching women. Applying it is crucial to rewiring your mindset.
Examples of Using the Win-Win Blueprint
You approach an attractive woman at a coffee shop. She smiles and gives you her number. Win!
You approach a woman who says she has a boyfriend. Instead of feeling rejected, you think “Win! I took action on my goals today.”
At a bar, you approach three different women. Two aren’t interested, one is. Instead of feeling like a failure, you celebrate going 1 for 3 as expected.
After an approach where the woman wasn’t interested, you turn to your wing man and say “That was an awesome approach! Blowouts don’t phase me.”
The core principle is feeling like a winner every time you approach by separating your self-worth from her specific reaction. This allows you to take consistent action with confidence.
Bonus Exercise: Desensitize Yourself to Rejection
Rejection desensitization is a process that involves intentionally seeking out and embracing rejection from women in order to become more comfortable with it over time. The goal of this exercise is to lessen the fear and emotional pain associated with rejection by experiencing it repeatedly in a controlled environment. The exercise is to go to a high-traffic area and aim to get rejected five times in a row. If someone responds positively, you must start over. The idea is to purposefully approach women, respectfully, but with the expectation of being rejected in order to build up a tolerance and emotional resilience over time.
When you assume attraction, you get attraction. When you assume rejection, you get rejection.
- Connell Barrett
Approaching Women: Tools of the Trade
The Five Master Steps
The “Five Master Steps” is a systematic approach taught by Barrett for men to approach and connect with women in an authentic and confident manner. Here are the five steps:
Make the Approach and Make it Often
When you go out to socialize with women make sure you initiate conversations with different women every 5-10 minutes at night and every 15 minutes during the day
This builds social momentum, helps you break free from overthinking, and overcomes approach anxiety
Give Genuine Value
Embrace your genuine self and express yourself without the need for pretense or seeking approval.
Flirt and show romantic interest (be “man-to-woman”)
Be real, be authentic rather than rely only on rehearsed techniques.
Have fun and be playful
Establish a Connection
Look for common interests and shared emotional experiences
Ask open-ended questions to understand what makes her fascinating
Share things about yourself to balance the conversation
Seize the Opportunity
Take action when you feel a connection whether it's getting her contact info, planning a date, or going in for a kiss.
Don’t settle for just a nice conversation, escalate things further
Lead the interaction by suggesting an “instant-date” if her logistics allow
Have an Attitude of Gratitude
After every approach, appreciate at least one great thing about it
Notice something positive, funny or a lesson learned
Focus on the good rather than being overly critical of yourself - every approach is a win
Fully commit to following these five steps during your designated approaching time, treating it like going to the gym. The more you put in the effort, the better the results.
Opening Techniques
There are two main types of openers when approaching women - direct and indirect openers.
Direct Openers Direct openers convey clear romantic interest right from the start. Some examples could be:
“Hey there, I wouldn't forgive myself if I didn't tell you how beautiful your smile was.”
“Hi, I just had to come over to let you know that your eyes are absolutely gorgeous.”
The upside of direct openers is that there is no ambiguity about your romantic intentions. The woman will immediately know you are interested in her in a romantic way. Many women appreciate a direct, confident approach. It can create an instant spark of attraction if she is interested as well.
The downside of direct openers is that some women may reject you outright if they are not available or in the mood for that level of forwardness. However, for women who are open to it, direct openers can be very effective at grabbing their attention and interest.
Indirect Openers Indirect openers start the conversation in a more friendly, casual way without explicitly stating romantic interest upfront. Some examples are:
“Where did you get that Starbucks, is it close by?”
“You look so into that book, it must be good. What's it about?”
The upside of indirect openers is that you avoid as many immediate rejections. They open the door to more conversations and opportunities to make a connection first before escalating to romantic interest.
The downside is that you can get stuck in the “friend zone” if you don’t transition to being more flirtatious and man-to-woman fairly quickly after the opener.
Conversation Tips
1. Balance asking questions and sharing about yourself
It’s important to strike a balance between asking the woman questions to learn about her, and also sharing things about yourself. Many guys make the mistake of just firing off question after question, turning it into an interview. That gets boring quickly.
Instead, after you ask her a question and she responds, share something related about yourself. For example, if you ask what she does for work and she says she’s a teacher, you could say “That’s really cool. I have a lot of respect for teachers. My sister is a teacher too and I see how hard she works.” This allows the conversation to flow more naturally back-and-forth.
2. Use open-ended questions to keep the conversation flowing
Yes/no questions tend to lead to dead-ends in conversation. Open-ended questions that start with what, why, how, etc. encourage her to share more details and keep things moving. For example, instead of “Did you have a good weekend?”, ask “What did you get up to this weekend?”
3. Be transparent about your intentions
There’s no need to play games or be vague about why you approached her. Women appreciate a straightforward, confident guy. Within the first few minutes, you can slip in a comment that makes your romantic interest clear like “You’re really cute, I had to meet you” or “I’m actually kind of introverted, but I saw you and just had to come say hi.”
Being transparent from the start allows you to flirt and connect as a romantic possibility, rather than getting stuck in the friend-zone. Of course, balance is key - you don’t want to come across as overly sexual. But letting her know you find her attractive early on is important.
How To Approach a Group Of Women
When you approach a woman who is out with friends or a group, it’s important to make a good impression on them as well. Her friends’ opinions will carry a lot of weight, so you want to get them on your side if possible.
Some tips for befriending her friends/group:
Make eye contact and introduce yourself confidently to everyone in the group. Compliment the group on something to create a friendly vibe.
Ask questions to engage her friends in the conversation and build rapport with them. Find common interests or connections you can discuss.
Don’t be overly flirtatious with the woman you’re interested in at first. Let her friends see you as a fun, likable guy before escalating the flirtation.
If her friends seem to approve of you, they are more likely to encourage her interest rather than cockblocking you.
If its a group of 4 or fewer women, address the whole group when approaching to avoid looking like you’re hitting on just one person.
If its a group of 5+, approach the one you’re interested in first. Compliment her in a fun way to get her attention, then have her introduce you to her friends.
How to Deal with Cockblockers
Even if you make a good impression on her friends, there may still be someone in the group who tries to cockblock you out of jealousy or protectiveness. Or some other fool at the bar, club etc. is interested in her and is trying to insert himself in your conversation to take her attention away from you.
Here are some tips on dealing with that:
For a jealous female friend, remain sincere and friendly, but unapologetic about your romantic interest in the woman. Her girlfriends likely want to see her meet someone.
For a jealous male friend trying to cockblock, create rapport with him through compliments, but don’t supplicate. You can even try introducing him to another woman as a wingman.
If another guy tries to interrupt and “steal” the woman you’re talking to:
Don’t panic. She is still interested in you, not him.
Politely let him know that it was nice meeting him, turn to her and resume the private conversation you two were having. If he persists, take charge and suggest moving to another part of the venue by saying for example, "Lets check out the dance floor" or "Lets go to the bar and grab another drink". Lead her there by holding her hand. He will either follow you, which will make him look like a stalker and make her feel uncomfortable, or he will stay behind, either way you win.
Advanced Dating Tactics
Barrett has no shortage of dating wisdom and advanced dating strategies. Here are some that he shares with his readers:
Getting her number in 60 seconds
The key is to be direct but charming. Suggest doing a quick “60-second date” right then and there to pique her interest. Compliment her in a non-creepy way like “You seem really fun, I’d love to get to know you better over a 60-second date right now if you’re up for it?” If she agrees, chat for a minute, make a flirtatious comment or two, then ask for her number before you have to run off. The time constraint makes it low pressure.
Initiating a ménage à trois (threesome)
Don’t blindside her with this out of nowhere. Bring it up early when things are still new and casual, after you’ve been intimate but before officially defining the relationship. Frame it as a sexy adventure you want to experience together, not just your own desire. A suggested text: “I’ve always wanted to try having a threesome with the right partner. I think it could be really hot and fun if we did it together. Would you be into that?”
Escaping the friend zone
Make a flirtatious comment that makes it clear you view her as more than just a friend. For example: “You look amazing tonight…” or “That little hair flip you just did was so sexy…” The key is making it a personal statement about her that sends a mild sexual/romantic impulse.
Reconnecting after getting her number
Send a playful “reconnect” text that jokes that you’ve been drifting apart as friends, even though you just met. For example: “I feel like we’re growing apart lately. It’s like I don’t even know you anymore! What happened to us?” This piques her interest again.
Charming a beautiful woman
Ask her about her nerdy/dorky side or past. The contrast between her beauty and that vulnerability creates a connection. You’re both being a little vulnerable together.
Using Instagram for dating
Curate an Instagram feed that showcases an adventurous, attractive lifestyle full of interesting hobbies and social life. Post photos and stories that create “FOMO” and make women want to be a part of the fun.
Leveraging social proof
Having a stylish female friend act as a “wingwoman” who socializes with you provides social proof. Or ask a mutual female friend to connect you with women she thinks could be a good match.
Right Person, Right Time
Barrett states that your goal should be finding the “Right Person, Right Time” situation. This means not settling for someone who is just “good enough”, but pursuing a truly great, compatible relationship.
To determine if someone is the right person at the right time, Barrett advises asking yourself three key questions:
Do you and this person simply “fit” together with natural rapport and compatibility? This means your personalities, values, and ways of relating just seem to mesh well together.
Do your major life goals and values align? This includes things like wanting or not wanting children, your moral/religious views, ambitions for the future, etc. Having mismatched core values can lead to major conflicts down the road.
Can you envision being able to grow together in the relationship over the long-term? Relationships require the ability to evolve and mature together as you both change over time.
If the answer is yes to all three of those questions, Barrett provides a seven-step process he calls the “Boyfriend Experience” to transition a dating relationship into an official committed relationship as girlfriend/boyfriend:
Build deep trust through open and honest communication with each other. Let your emotional walls down.
Integrate her into your social circle by bringing her around your friends and family. This allows her to see how you fit into your community.
Do activities together that boyfriends and girlfriends typically do, like going on day dates, making dinners together, attending events as a couple, etc.
“Man up” and take on traditional masculine roles that make her feel cherished and protected, like being physically fit, fixing things around her place, taking charge on decisions, etc.
Show your generous and caring side, like tipping well at restaurants, doing volunteer/charity work together, and making gestures of service.
Have a recurring weekly “date night” to ensure you’re prioritizing quality time together.
After 1-2 months of consistently doing these things, have an explicit conversation asking her to be your exclusive girlfriend in a committed relationship.
Conclusion
Dating is all about having fun and spreading positive vibes. Enjoying the process and being yourself can boost your confidence and help you take more chances in romance. When dating is enjoyable, you're more likely to do things that lead to good outcomes, making you feel better about yourself and keeping you motivated. Having a great time while dating is crucial - it starts a chain reaction of good experiences. Being proactive and getting excited about possibilities builds momentum and increases your chances of success. This positive cycle helps you overcome challenges and leads to a more satisfying dating life.
To make dating fun, it's important to be genuine and open with others. Sharing your true self can create deeper connections with potential partners. Having supportive friends or wingmen around can make meeting new people even more enjoyable. Engaging in playful activities like sending funny messages or bantering with dates can also add to the fun.
Finding joy in small things and bringing humor into your interactions creates a relaxed atmosphere that makes dating feel natural and enjoyable. This approach helps reduce stress and awkwardness, making the experience more pleasant. Successful dating comes down to having a positive attitude and embracing the journey with an open heart. By focusing on creating a fulfilling experience for yourself and others, you increase your chances of forming meaningful connections and finding love. So go out there, have fun, and let love find its way to you!
We hope you enjoyed our summary of Connell Barrett’s “Dating Sucks, but You Don't: The Modern Guy's Guide to Total Confidence, Romantic Connection, and Finding the Perfect Partner.” If you're eager to dive deeper into the key concepts and actionable advice presented in this summary, we encourage you to consider purchasing the original book which you can do by clicking here. You can also check out Connell Barrett’s website here and podcast here for more great dating advice.