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How To Be Persistent With a Woman Without Being Annoying

How To Be Persistent With a Woman Without Being Annoying

Want to learn how to be persistent with a woman without being annoying? You’ve come to the right place. There’s a fine line between persistence and desperation in dating. Being too clingy will scare a woman off but being too aloof, will cause her to forget you.

In this article, we’ll discuss the difference between persistence and desperation. I’ll show you examples of annoying messaging and compare them with examples of more persistent communications. You’ll also learn persistence hacks that keep your mindset in a positive and controlled mental state. We’ll touch on ways to persistently close for a compelling date. And, you’ll learn what to do to come across as confident, rather than annoying. Lastly, we’ll discuss common mistakes men make that cause them to look desperate and how to avoid them.

Now, without further adieu, let’s dive into the many ways you can avoid becoming a stage-5 clinger, while also demonstrating your persistence. First, let’s discuss the difference between persistence and desperation.

How to Be Persistent with a Woman Vs. Being Annoying

Persistence follows a predictable and replicable cadence while desperation does not. Desperation is different than persistence because it stems from the need to control others. Feeling out of control can trigger a person with an anxious attachment style to become needy, clingy, and even violent.

The Persistence Formula for Messaging

The persistence formula I follow when coaching clients on how to get women to respond on dating apps is as follows. Always send a minimum of 3 messages before calling it quits, the initial message (initial), the follow-up message (FU), and the last-ditch (LD) message.

Some apps won’t allow you to follow up, and that’s fine. But, if you’re able to, always follow up at least 3 times. There are some salespeople who will tell you to follow up more than 5 times, which works if you’re tracking your outreach and see a good return on your time investment. Three has always seen the best returns for me, and I’ve been using this strategy effectively for years, both in dating and in business.

The Initial Message

To explain in greater detail, first I recommend you send a woman an initial message. Your initial message should speak to something emotionally compelling on her profile. Keep it to one sentence and end in a question. The message should also add value, which is a complex topic that I won’t be able to discuss thoroughly here. I teach exactly how to do this in my Signature program, which you can learn more about by watching my webinar.

Once your message is sent, give her time to respond. For this, I usually wait 48 hours for a reply back. If I don’t hear from the person after 48 hours, which happens between 70-90% of the time, then I send a follow-up message.

Pro-Tip: Never assume that no response means no interest. There are millions of reasons why a woman doesn’t respond and many have nothing to do with you. Don’t give up after the first try. It’s important to persevere.

The Follow-Up (FU) Message

The follow-up (FU) message, brings my previous note to the top of that person’s queue. Keep this message super simple, and never call out bad behavior by saying something like, “you never responded.”

The FU message is a quick reminder for her to read your first message and respond. My FU message usually sees a lower return than my initial message, but it serves the purpose of putting enough time between my initial message and my last-ditch (LD) message.

The Last-Ditch (LD) Message

Again, I wait 48 hours in the hopes that they will respond, but I expect them not to. As such, I generally send an LD message 48 hours following my FU message.

Persistence Hack: Turn Off Notifications

Instead of waiting on the edge of your seat for her to respond and then diving for your phone when she does, put yourself in the driver’s seat by turning off your notifications. This allows you to remain in control of your dating apps, not the other way around. Check back in once a day and respond on your schedule, not anyone else’s. Doing so will demonstrate your value and make you seem harder to get.

I like this strategy because it’s not about playing games, it’s about controlling your mindset. Schedule your dating app messaging for a 30-minute window at your most confident time of day. Try adding a recurring calendar event for dating app time after you’ve had coffee, lifted weights, or eaten breakfast every morning.

Examples of Desperate Messaging

Calling A Woman Repeatedly

Trying her from different numbers, and tricking her into answering, is not persistence, it’s desperation.

Why It Doesn’t Work

Calling a woman repeatedly demonstrates that you are insecure and hungry for control. This behavior suggests a lack of confidence and an inability to understand what might be happening for the woman. Exhibiting this type of behavior is also suggestive of future control, manipulation, and domestic violence.

In essence, she’ll see the writing on the wall for any future relationship. An inability to control oneself suggests mental instability, a trait that a woman does not want to pass down to future children.

Texting Her Long Messages

Sending a woman long messages over and over even when she barely responds or doesn’t respond at all is desperate.

Why It Doesn’t Work

Healthy relationships require equal emotional interest and investment. If you’re sending huge paragraphs, it’s likely you’re dominating the conversation in other ways as well. It’s a bit selfish to talk without asking questions that require a thoughtful response. This type of conversation is boring because it adds no value to the receiver’s life.

Sending Love Letters Too Soon

Writing long love letters when a woman asks you to stop, is desperation, not persistence.

Why It Doesn’t Work

When a woman asks you to stop doing something respectfully, listen. Continuing to engage in behaviors that a woman has explicitly stated make her feel uncomfortable, will not win you more affection. One of the most powerful conversation skills is the ability to listen and remain present in the conversation.

Thinking only about what you will say next or what you want out of the dialogue is a one-way street that is guaranteed to lead to failure. Additionally, unsolicited love letters are usually more about the sender’s state of mind.

If you’re doing this too early on, she’ll doubt your sincerity, and rightly so. Is it that you love her so soon? Really? Or is it something else? Likely, what is appearing is an insecure attachment style, otherwise known as an anxious attachment style.

Anxious Attachment

Attachment styles are stable but can be changed with proper help from a professional. I work with every client on attachment in my Signature program and it’s an important topic to understand thoroughly when dating. If you notice you’re feeling the urge to write long love-letters before you’ve really spent much time getting to know a particular woman, I recommend booking a session with a coach or therapist.

It’s important to catch an anxious attachment as soon as possible because this type of desperation can easily lead to stalkerish behavior and make a woman feel as though she’s in danger (maybe she tells you things are moving too fast). It’s super scary for women. Don’t do it. Read the book Attached if this is happening.

Never Use Annoying Language in Your Texts/Messages

Don’t call out bad behavior. Remember, you catch more bees with honey.

how to be persistent with a woman you're datingWhy It Doesn’t Work

Calling out bad behavior makes a woman feel like you’re her dad, and that ain’t sexy. A grown woman doesn’t want to be reprimanded. While you may be upset that she hasn’t responded, don’t always assume it’s intentional.

I like to assume whatever is in my own best interest to avoid getting upset based on a fallible assumption. Why assume she is intentionally ignoring you when the belief itself lowers your self-confidence? I’d assume that something interrupted her, the message did not go through, burglars stole her phone or something else that doesn’t negatively impact your confidence. Sometimes being ignorant or slightly narcissistic can help.

how to be persistent with a woman Why It Doesn’t Work

The above message demonstrates that you have one-itis and are desperate for her attention, which is not sexy. If you’re actively worried about her not texting you back, it’s a sign that you need to MegaDate stat. MegaDating is the process of dating multiple people at the same time to diffuse your energy, increase your confidence, and avoid becoming a stage-5 clinger.

Annoying Message Example: What are you doing right now? I know you're off work.Why It Doesn’t Work

The above message screams psycho. How would you like it if a woman sent it to you? Sending a message like this tells her you’re a control freak who is mentally unstable. If this is happening, I strongly encourage discussing it with a counselor or coach. Continuing down this path will not return you the love that you’re craving.

How to Be Persistent with a Woman when Messaging

Always use persistent language in your messages to women. Below are several examples and why they’re effective.

Persistent Message Example: I want to take you on a date.Why it works

Being direct demonstrates confidence. Expressing your wants is an indication that you have a healthy communication style. People who are unable to communicate their wants and needs to others, fail to get what they want out of life. Additionally, when you’re unable to clearly communicate your wants and needs, then you gradually build resentment for others because they can’t give you what you want.

how to be persistent with a woman exampleWhy It Works

It’s truthful and gets to the point. After all, you didn’t sign up on a dating app to spend hours sitting alone at home texting women you’ll never meet IRL. Don’t be afraid to be direct.

Persistent Message Example: I want to see if we'd click in real lifeWhy it works

Again, this message is honest and direct. For the same reasons above, this message is powerful.

how to be persistent with a woman Why it works

Similar to the messages above, this message powerfully and simply communicates intent. Expressing that you want to see what she is like IRL, gives your statement an outward focus that speaks directly to the receiver. The message also subtly challenges her to meet you because it doesn’t express insecurity like “I think you’re perfect” or “You’re beautiful.”

You’re not complimenting her by saying you want to see what she’s like. Instead, you’re conveying the fact that you’re interested in seeing if you like her. On the flip side, if you expressed the belief that you already liked her, or thought she was beautiful or perfect, you would be conveying desperation because you don’t know her yet.

Persistent Messaging: I want to meet you in person.Why it works

The above message works because of its simplicity and honesty. Being direct demonstrates your confidence and the fact that you’re not afraid to go after what you want in life, a very attractive quality.

Persistent Messaging: I want to know what it would be like to go on a date with an Israeli woman.Why it works

Honest and interesting. This message creates a subtle challenge for a woman because it makes her feel as though she’s somehow representing all Israeli women by meeting you. She certainly wouldn’t want to make a bad impression if her cultural heritage is on the line.

how to be persistent with a woman Why it works

Saying “I want to meet you” is different than saying “let’s meet” because it doesn’t make any assumptions about her interest. “Let’s meet” is fine to say and can be powerful because it subliminally creates the feeling that you’ve known her for a long time because you’re just assuming she wants to meet you.

An even more powerful message is to say “I want to meet you” because it states your wants without assumption and puts the ball clearly in her court. Follow it up with a TDL and she’s bound to say “yes” to a date based on your confidence alone. Practice communicating your wants in every area of life. Are you asking for what you want at work and with family and friends? It’s a powerful move.

Be Strategic with Your Messaging

If your prospective date takes 3 days to text or message you back, the last thing you want to do is respond to her the moment she messages you. In this case, wait a few hours then text her back. Keep in mind if you have “read receipts” showing in your cell phone, then you’ll need to not open up the message, otherwise, she’ll see when you opened it.

Always Use TDL’s When You’re In-Person with Her

If you’re dating this woman in real life, always be probing for her interests. This will help you set up the next date while you’re still on the current date with her. This is the ultimate persistence tactic as it SHOWS the woman you want to see her again.

Examples of TDL Situations

Her: She says she’s always wanted to try kite-boarding.

You: You say ‘Great, let’s go on Saturday at 11.’

Her: She says she’s always wanted to visit Alcatraz.

You: You say ‘Great, let’s go on Saturday at 11.’

Her: She says she’s always wanted to try pottery-making.

You: You say ‘Great, let’s go on Saturday at 11.’

Are you catching the pattern here?

Don’t Message Her Right After Your Date

Give her space to get curious about you. A guy I dated in my 100-Date Experiment texted me 30 seconds after our date, which killed the sexual tension. You need to give her a little time to think about how she feels towards you. Whatever you do, don’t text her right after your date.

Do Call Her 24 Hours Before Your Date to Confirm

Here’s your chance to let her know you’re excited to meet her on your next date. Keep your message short and sweet.

Try this: “Hey Jane, it’s John. Looking forward to our date tomorrow. I’m actually going to be running errands in your area beforehand. Why don’t I swoop you up at 10:45?”

Be Prepared To Overcome Her Objections

If she says she’s busy at 6 pm, try an alternative time. If she can’t do the day you proposed, change the day. If she can’t make it to the location in your TDL, try an alternate location. Always be prepared with plan B and C so you’re ready to overcome predictable objections.

You also want to get good at pitching your dates so they sound as though they’re a once-in-a-lifetime opportunity. I teach my Signature clients how to do this in greater detail but let’s keep it simple here. Always make a minimum of 3 attempts to overturn her objection before calling it quits. Women subconsciously test men to see whether they are persistent enough to get what they want. Women want men who are courageous, and persistence is a clear demonstrator of this valuable trait.


I hope this short guide on how to be persistent with a woman has pointed you in the right direction. Just remember, the primary difference between being persistent and being annoying comes down to managing your mindset. Creating a duplicable system can help to quell anxiety and avoid desperation. My personal formula is to send three messages minimum before calling it quits. The first message is the initial message. The second message is the follow-up. And, the final message is the last-ditch.

Don’t call out bad behavior when messaging or following up. Remember, you catch more bees with honey. Turn off your notifications and schedule 30 minutes on your calendar each day for dating app time. Doing so will help you remain in control of your mindset.

Communicate your wants and intentions directly and transparently. Don’t try and beat-around-the-bush. A woman cannot read your mind. Acknowledge when you’re feeling needy or desperate and consciously shift your focus by reaching out to friends and family, scheduling a fun activity, or MegaDating.

Anticipate her objections and be prepared to overcome them by having a solid back-up plan. Invite her on a compelling TDL 3 days in advance of the date. And, be sure to confirm the date either the day before or the morning of. Avoid the use of annoying language when messaging and try to limit messaging as much as you can. Too many messages kill mystery and lead to more ghosting, flaking, and friend-zoning.

Close for the second date TDL while you’re with her on the first date. And, don’t message her immediately after the date has ended. Give her time and space to think about you and become more curious.

When in Doubt, Hire Some Help

It’s always helpful to work with a trusted mentor who has been there and done it before. If you’d like to boost your sexual attraction and avoid getting too needy with a woman you are dating, consider hiring an expert. Having someone to bounce ideas off of, who has a solid outside perspective of what’s happening can be the boost you need to win her affections. It’s also helpful to talk to a woman to better understand the female mind. Check out my webinar to see how private, one-on-one coaching can help you attract your most ideal girlfriend.


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