The Bold Woman's Guide to Approaching Men

Understanding What Men Want

Men appreciate women who:

• Take Initiative: Most men find it attractive and refreshing when women make the first move
• Are Direct: Men often miss subtle hints - being clear about your interest is helpful
• Show Genuine Interest: Ask questions and listen to his answers
• Are Confident: Confidence is universally attractive
• Have Their Own Life: Independence and having your own interests is appealing

Breaking the Ice: Making the First Move

1. The Power of Eye Contact and Smiling

• The Look: Make eye contact, smile, then look away. Do this 2-3 times
• The Smile: A genuine, warm smile is incredibly inviting
• The Wave: A small, friendly wave can give him the green light to approach
• If He Doesn't Approach: That's okay - you can approach him instead

2. Starting the Conversation

Casual Openers:

• "Hi, I'm [name]. I saw you from over there and wanted to come say hello."
• "I noticed you and thought you had great style/energy/smile."
• "This might be forward, but I'd regret not introducing myself. I'm [name]."

Situational Openers:

• At a bar: "What are you drinking? I'm trying to figure out what to order."
• At the gym: "Sorry to bother you, but can you spot me?" or "What's your workout routine?"
• At a bookstore: "Have you read anything good lately?"
• At an event: "What brings you here tonight?"

Compliment Openers:

• "I love your shirt/watch/style. Where'd you get it?"
• "You have a great smile."
• "I couldn't help but notice you - you seem really interesting."

Building Attraction

Be Playfully Flirty

• Light teasing (nothing mean-spirited)
• Playful challenges: "I bet you can't guess what I do for work"
• Gentle physical touch (on the arm, shoulder) when laughing
• Hold eye contact a moment longer than usual

Show Interest in Him

• Ask about his interests and passions
• Let him share his stories
• Ask follow-up questions that show you're listening
• Compliment his accomplishments or qualities, not just his looks

Share About Yourself

• Talk about your passions and what excites you
• Share interesting stories from your life
• Show your personality - be authentic
• Balance the conversation - don't interview him, have a dialogue

Reading His Interest Level

He's Interested If:

• He's making consistent eye contact
• His body is facing toward you
• He's asking questions about you
• He's laughing at your jokes
• He finds reasons to touch your arm or shoulder
• He's leaning in when you talk
• He's not checking his phone
• He's asking if you're here with anyone

He's Not Interested If:

• One-word answers
• Looking around the room frequently
• Body angled away from you
• Mentions his girlfriend/partner
• Checking his phone repeatedly
• Trying to flag down friends

Getting His Number (Yes, You Can Ask!)

Direct Approaches:

• "I'm really enjoying talking to you. Can I get your number?"
• "We should continue this conversation over coffee. What's your number?"
• "I'd love to hang out sometime. Want to exchange numbers?"

Playful Approaches:

• "I don't usually do this, but you seem cool. Give me your number."
• "Here, put your number in my phone" (hand him your phone)
• "Let me guess your number..." (joke around, then ask for the real one)

Activity-Based Approaches:

• "You mentioned loving [activity]. We should do that together sometime. Number?"
• "I know a great [restaurant/bar/place] for [thing you discussed]. Give me your number and we'll plan it."

The Art of Asking Him Out

Be Direct and Confident

Men appreciate directness. These work well:

• "I'd like to take you out for drinks. Are you free this weekend?"
• "Let's grab coffee this week. Thursday work for you?"
• "I'm checking out this new restaurant Friday night. Come with me?"

Make It Easy for Him

• Suggest a specific day and time
• Pick the venue (but be open to his suggestions)
• Make it clear it's a date, not just hanging out
• Keep the first date casual and low-pressure

If He Says No

• Take it gracefully: "No worries! Hope you have a great week"
• Don't take it personally - there could be many reasons
• Be proud that you took the initiative
• Move on - the right person will say yes

Different Settings, Different Approaches

At Bars/Clubs

• Buy him a drink - men rarely get this and will appreciate it
• Ask him to dance
• Use the loud environment to get closer for conversation
• Be aware of liquid courage - stay confident but not overly intoxicated

At the Gym

• Ask for a spot or form advice
• Compliment his workout technique
• Start conversations in common areas, not mid-workout
• Respect gym etiquette - keep it brief if he seems focused

During the Day (Coffee Shops, Stores)

• Men are often surprised by day approaches - be confident
• Context-based openers work great
• Keep the initial approach light and friendly
• If he seems receptive, extend the conversation

Through Friends

• Ask your mutual friend about him first
• Attend group hangouts where he'll be
• Ask your friend to introduce you or facilitate
• Mutual friends give you instant credibility

Online (Dating Apps, Social Media)

• Be the first to message - it shows confidence
• Reference something specific from his profile
• Ask an interesting question
• Move to in-person meeting relatively quickly

Common Concerns (And Why They're Not Issues)

"Will He Think I'm Desperate?"

No. Men see confident women who know what they want as attractive, not desperate. Desperation is needy behavior after rejection - approaching confidently is the opposite.

"Will He Lose Interest If I Make It Too Easy?"

No. Healthy men appreciate when women are clear about their interest. Games and playing hard to get often just create confusion. Be authentic.

"What If He Rejects Me?"

That's okay. Rejection happens to everyone. You'll survive it and be proud you tried. Every rejection gets you closer to the right person.

"Should I Wait for Him to Make the First Move?"

Not necessarily. If you want to meet him, make it happen. Why wait and potentially miss an opportunity? Modern dating rewards initiative.

After Getting His Number

The First Text

• Text him the same day or next day
• "Hey! This is [name] from [where you met]. Great meeting you!"
• Reference something funny or interesting from your conversation
• If you asked him out, confirm the plans

Planning the Date

• Since you initiated, it's nice to plan the first date
• Choose somewhere you're comfortable
• Pick a place conducive to conversation
• Be open to his input - it's a collaboration

Who Pays?

• If you asked him out, offering to pay is a nice gesture
• He may insist on paying - let him if he wants
• Splitting is also perfectly fine
• What matters is the connection, not who pays

Red Flags to Watch For

Even if he seems interested, be aware of these warning signs:

• He's Vague About His Life: Might be hiding something
• Only Wants Late Night Hangouts: May only want something physical
• Pushes for Your Place: Right away without building trust first
• Talks Negatively About Exes: May have unresolved issues
• Love Bombing: Over-the-top affection too soon is a red flag
• Disrespects Boundaries: Pushes when you say no

Mistakes to Avoid

• Being Too Aggressive: There's a line between confident and pushy
• Using Too Much Alcohol for Courage: Be confident sober
• Playing Games: Be straightforward about your interest
• Oversharing Too Soon: Keep some mystery initially
• Talking Only About Yourself: Balance the conversation
• Being on Your Phone: Give him your full attention
• Pretending to Be Someone You're Not: Authenticity wins