Get Him to Indirectly Ask You Out (Or Be Direct)

Know When to Move It Offline

Whether you’ re on a dating site or dating app, you need to keep the message flow going once he’ s responding to you.

I know, I know…you want him to make the move and be direct. But you do know that we outnumber men. Waiting for him to come around when he has more options than you do. Well, the early bird gets the worm. And I want you to have his attention and guiding it in the right direction. That direction is into the relationship you want.

Use this easy formula to keep the conversation progressing towards getting you a date:

  1. Ask him questions.
  2. Answer it yourself –he’ s curious about you, too.
  3. Guide those questions in the direction you want, by asking questions that steer in that direction.

One of the biggest mistakes a lot of Sugars make is once they start talking to a potential Sugar Daddy they leave it in the hands of the Sugar Daddy.

No matter what site or app you’ re on, weeks of back and forth messages isn’ t going to get you what you want.

He might have lost interest and moved on – no one joins these sites to find a pen pal. And if youare finding yourself being a pen pal to many. Well, let me break the news to you….

You are not his priority and he’ s keeping you around in case the one he is taking to and getting to know doesn’ t work.

But at the same time, you don’ t want to push for the date too soon.

You want to spend some time building a connection, trust, and attraction.

After about 3-4 messages it’ s time to move it offline. I’ m not counting an instant chat session of messaging back and forth. But you should realize that, to become a reality you should move the chat conversation to the phone.

Here is a primer on getting him to take you out on a date:

  1. Make a comment about how you’ d like to get to know him better by talking in person.
  2. Avoid the word date, I repeat AVOID the word date. Opting for other words like “meet up” or “get together”.
  3. Finally, make sure you offer suggestions. So you have started on the right foot.Profile – check!

So you have started on the right foot.

Profile – check!

Photos – check!

Icebreaker messages – check!

The conversations are engaging and they are responding and you are sure pretty sure they’ re into you.

It’ s time to move the conversation offline. To either the phone or in-person date.

You don’ t want to rush it, but you also don’ t want to end up as the Sugar Baby Pen-Pal.

By asking for a date, it will help you weed out who is serious too!

There is no need to keep speaking with someone for months without having met. Otherwise you will end up wasting your time.

Some might disappear. That’ s okay. Your focus is attracting your ideal Sugar Daddy. After all, it’ s the reason of why you are here.

Here are some tips to get the date…

Realize that timing is EVERYTHING.

If you lack engaging conversations and respond back with “yes” or “no” type of responses. Or interviewing them. He can lose interest. Nobody wants to feel like it’ s a chore to be with you based on the impressing you are giving them of you with a list of questions.

As he’ ll lose interest and move on.

But if you come on too strong, you’ ll turn him off.

Once you understand how to move the conversation along, you’ ll be in the driver’s seat.

So a successful messaging sequence looks like this:

  • You break the ice with an intriguing and enticing copy & paste message.
  • He responds.
  • You respond to his message, ending with a personalized question inspired by something he said in his response or profile (but you are guiding the conversation along)
  • He responds again.
  • You respond to what he said and then ask to meet. (Plus, he’ ll know you are comfortable based on your readiness).

Are there exceptions to this? Of course.

If you’ re carrying the majority of the conversation and his answers seem short, not engaging, or nonresponsive, you’ ll want to keep the exchange going a little longer.

Get in his head with some Sugar Daddy Psych 101

Based on his situation, he needs to feel comfortable meeting you in person if he’ s married.

Some people click faster than others. And the more we feel connected, liked by, or attracted to someone, the more persuasive they become.

So basically, your Sugar Daddy will feel more comfortable with you when you captured his curiosity and he feels a certain comfort with you.

Don’ t think because he is on a Sugar Daddy dating type of site that he is on board to meet you right away. He has doubts, just like you. He’ s wondering if she’ s real, can he trust her etc.

And if he is someone who is known. Well, he has a lot to lose. And especially if he is married.

By pulling his emotional triggers to get him to see himself in you based on why you are here. Will make the process go faster.

Sugar Tip: (Marketing 101 – Reminder) You are seeking a Sugar Daddy because you “want”something from him. You can’ t sell your issues/needs. You must sell themselves on you as the one for them. Your SD is there for a reason. Why do you think your ideal SD is seeking you? Take a moment to step into your SD’ s shoes and now write about you in the way your SD is wanting to find someone like you.

You can make him feel comfortable with you by getting inside his head and mimicking the style in which he communicates to you.

This is called “mirroring,” and it’ s easier than you think.

Here’ s how to do it (check out the ‘ Sugar Persuasion – Bag O’ Tactics’ for more on mirroring:

  • Copy the way he opens his message when you respond. If he writes, “Hey, Taylor”, greet him with “Hey, Richard”.
  • Mirror his message length. If he sends three sentences, you send about three sentences. If he only replies with a few words, keep your next message pretty concise as well.
  • If he’ s using “LOL” and smileys, you probably should too. (Just don’ t go overboard with it; 1-2 per message max.)

Recognize when he’s ready to meet you

The trick is to pay attention to what, how much, and in what tone he’ s writing.

If you’ re lucky, he will send you a message that practically screams, “I’ m into you.” In this situation, you might even provide you with his number. And be quick himself.

Don’ t get scared off by it, if you are not ready. But you can’ t wait and string him along because he can be engaging in conversation with other women who are eagerly ready to go on a date with him. Some SD’ s move fast and some don’ t. You’ ll have to adjust your speed if they are ready to meet you, or they’ ll lose interest if you don’ t. Because they might feel as though you are talking to other people or you are not into them.

You will know that he is really digging you when he …

  • He sends you long(ish) messages. If you sent him a few sentences and he replies with something of the same length or longer, he’ s usually pretty interested
  • He’s giving you !!!’s and ;)’s. Emojis and lols and you know what it means…he’ s in to you. But sometimes older men can go overboard with this and try to come across as hip too.
  • He’s asking you questions. Curiosity is a good sign –he wants to know more about you.

Insecurity, on the other hand, isn’ t sexy at all. Saying something like, “I can really use some help financially to pay my bills and for school”…. Without getting to know them will come across as desperate.

Keep it casual.

Suggesting a meet-up is far different than suggesting a date.

Yes, we all know it’ s practically the same thing, but the word “date” sounds a lot scarier. You haven’ t even met yet – how can you really even be going on a date?

Plus, it’ s a high-investment, emotionally charged word. “Meeting up” is more laid-back, casual, and safe.

You might be wanting to have him pay for your first date. And take you shopping as a nice gesture. But think of your date as meeting up to see if you like each other.

This puts less pressure on both of you. As you wouldn’ t want him to have you meet him at the hotel to take you for a test drive to see if you have sexual chemistry.

Plus, if things don’ t go well, you haven’ t invested in a lot of time. And if the meetup is going well, you can extend it out.

If you suggest shopping without him bringing it up, he’ ll be thinking, “If I don’ t like this girl, I’ ll be out money without getting back a return!”

Make statements he already agrees with.

You’ ve heard the phrase “it’ s not what you say but how you say it.”

This definitely rings true when asking him out. Say something you KNOW he’ ll agree with, because small yeses help lead up to the BIGGER yes. And it also helps with planting those seeds to get what you really want and for him to say yes.

Here are two examples:

  • “Let’s get together for coffee or drinks sometime soon. Talking in person just seems like a MUCH better way to get to know someone than messaging online…what do you think?”
  • “You seem interesting, but I’ve found it’s difficult to predict chemistry until you meet someone in person. What are your plans for the upcoming week and weekend?”

Who wouldn’ t agree that talking in person is a better way to get to know someone than exchanging messages online?

Or that it’ s easier to predict chemistry in person than online?

Whatever you do, don’ t just ask: “Want to take me out on a date?”

Stay in the driver’s seat.

Once you get confirmation, you want to set a time and date.

Don’ t EVER leave it completely open for him to choose when and where.

What you can do is suggest a few options.

For example: “Perfect, how about Wednesday evening or Saturday afternoon?”

This gets you in the direction of getting him to commit to meet up and figuring out the “When & Where?” to make it happen.

You want to keep his attention focused on meeting up.

Anything else can be discussed in person.

Why take any unnecessary risks right as the deal’ s about to close?

Don’ t forget to exchange phone numbers and suggest that he send his so that you know it’ s him and “in case something last-minute comes up” on either end.