First dates: Fun ways to ask critical questions when dating for marriage

Hello, Gorgeous!

Ahhh the money question. How do we broach such a topic?

I am so uncomfortable. I don’t want to seem like a gold digger or a b*tch.

An It Girl is never afraid. As a matter of fact, she is fearless because she knows what she wants. She weeds out the weak with her weed whacker on the first try. Or a first date. 

When dating with marriage in mind, the goal is not to exclusively ask whether someone has aligned interests or is entertaining. 

These queries will help you understand their 

• Character
• Values
• emotional maturity
• Lifestyle
• and ability to potentially build a life with you. 

There is a fun, gamified way to enquire on a first date with an eligible suitor.

Not every date is all job interviews and transcripts. Save that for the office. 

It Girls are experts in expressing themselves and making others feel included as a natural part of the dialogue. They fish for information with conviction and levity. 

On a first date, she is essentially a princess. Kind, gracious, and hospitable. Think Princess Diana in her sweatshirt and cycling shorts. That is the energy I want you to give on an initial meeting even though you might be in a gown. Especially if it is after 6pm. 

Remember, questions do not have to be questions. 

They can be amusing prompts. 

Example 1: Every time you take a sip of your glass, you have to tell me your favourite something or simple pleasure.

Example 2: Top 5 favourite film directors. Go.

Example 3: Every time I tell a funny or abysmal date story–you share one and we go back and forth.

Example 4: Let’s play a game of red flag, green flag, beige flag.

Example 5: Tell me something about you that would surprise most people. 

See? It does not have to be all leather straps tying you down for melted candle wax and syringes. Torture can be turned around into delightful conversation as long as you are your pleasant It Girl self. Jests and japes not included. 

Here are critical questions to ask when dating for marriage.

My favourite of all is the money question. The Money Lite version. 

This can be peeled back later on in detail to discover each other’s goals, but I like to frame it in the sense of results of success rather than ‘What are steps you are taking to get there?’ Boring. 

You will organically learn this with time by seeing how a man lives and be certain to bring this up early. If you are in your 30s+, it is most likely he is already on his way to success with establishing himself in a career or enterprise he is proud of. 

This is easier to tell than anything. Especially when you visit his home and explore his daily, weekly, and seasonal routines. Not to mention his social circle amongst a plethora of circumstances he will be facing on future dates. 

If all your bills and taxes were paid, what would you do with your life? 

How would it look day to day, night to night? On holiday, during the weekdays. The more specific each scenario–the better. This means he has envisioned his goals clearly and has reverse engineered his way to bring it to fruition. If he is vague, ask him to get specific. 

This way you can gather a sense of his dreams and dream yourself as big as you want. Then dream even bigger. The answer to this will tell you his aspirations and intentions right off the bat. 

If he does not have the emotional intelligence to ask you the question back, tell him your answer after he does. Without prompt. 

Sometimes people have brief moments of their head being so far up their own butts, it happens. Not intentionally but you are getting him to dream, so he is deep in the fantasy and that is okay. Let it slide. At least on the first prompt. 

If he does not mention a family–you can ask him. He cannot read your mind. Also, you have a mouth, don’t you? Use it kindly to your advantage to find what you need without wasting time. A simple Does this include a family one day? will guide both of you into deeper discussions. 

You will find that some goals seem simpler than others such as having a family to celebrate every chapter with or to make something of themselves to create an enriching extensive lifestyle. It is up to you to decide your preferences based on his remarks. 

How do you handle conflict?

This was a recently painful one that could have not been so excruciating if I was simply face to face with my sweetheart. 

Heads up: If you cannot be in person for handling conflict, FaceTime or talk on the phone so no inflections are misconstrued through the abyss of lamentable texts.

I have a tendency to be out of pocket and blurt out the honest truth in a way that makes people laugh. They laugh because it is true. Caveat: There is a careful way to do this that takes active consistent practise. 

You can use this as a dangerous weapon in your arsenal and blatantly ask if someone is a hothead up front. Do not waste your time, because you do not want Medusa rearing her ugly head in his voice-raising outbursts. 

Can you handle his emotional or logically silent displays with patience? Do you want to handle this? This is imperative for prevailing the throes of tribulations. LEARN THEM NOW. 

What are your love languages–in order?

I maintain levity by answering ‘Acts of food’. Because it is true. 

However, some unaware individuals or those from foreign cultures might not see this as important. You can briefly explain it without it being overwrought or have them take a free quiz online later. This is not do or die but it helps, so do not grow upset if someone does not immediately comprehend this notion.

Love languages are so that affection does not fall upon deaf ears. Both of you will appreciate being loved in different ways (possibly–everyone is different) and each method is applied appropriately. 

If you have most of these in common in a similar order – fantastic! You have someone who will immediately understand you without the efforts of extraordinary clarification. 

Caveat: These might change over time as you experience more.

Cardinal rule: Pressure does not make diamonds on a first date.

This is simply meeting and getting a feel for who the other person is. Whatever happens during this meeting DO NOT PRESS OR STRESS SOMEONE FOR ANSWERS. Keep it light. 

You never want people walking away from you feeling uncomfortable or down. Others are to always walk away feeling better after having spent time with you. They should be invigorated dreaming about you later and thrilled to chat some more. 

To the point that you might have to shut down a cell tower somewhere and his friends have to rip his phone from his hands. 

Never settle. He is out there. 

I see so many women who are living the dream life reminding me to never settle. Saying ‘there is someone for everyone’ sounds like something we have heard repeatedly but because it is true. There is the person there you need in the moment for the right time and place. Then, there is someone who has all the things you want that you would like to keep around forever.

All spoken from my loved ones who are freshly married, newly given birth, and those who have been living the dream for decades. Never stop choosing the right words to bring out the best in him, and you will always choose each other.

An It Girl does not fear difficult conversations. She creates them with grace.

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Date with intention. Choose with confidence.