Tessa Mac

This is a VERY common question I get as a dating coach. I’ve thought about this topic extensively and typically it is the result of 1 of these 5 reasons:

1) Lack of genuine curiosity: 

It’s very hard to ask someone interesting questions when you’re not particularly interested in them (beyond, perhaps, being physically attractive). Asking someone what their family is like, for instance, isn't a "bad" question, in itself but it also might not be authentic as far as what you actually care about. (See point 5 as well as there may be overlap).

Solution: Be honest with yourself about what you actually like (or dislike) about the people you've been on dates with. If you discover they don’t generate curiosity, then consider exploring why, and also, raising your standards to becoming  more selective with who you go out with.

This may mean less potential dates, so there can sometimes be a self-worth piece to explore here (different rabbit hole). In these cases, more is not more. 

2) Fear of going “off script” and asking bolder, deeper, questions:

Solution: If you are a super beginner and  want some help with this, I STRONGLY recommend you buy this game to play with your next date: https://www.werenotreallystrangers.com/collections/games/products/not-really-strangers-card-deck

3) Feeling nervous and unprepared: 

Sometimes we mistake questions for the source of the problem when really it's a symptom of anxiety and wanting to be liked by your date. 

This is another topic I can expand on upon request. The short answer is creating a ritual that sets yourself up for success on a date SO THAT you go into it having made as many decisions as possible, which eliminates anxiety (something that only exists in the future). 

Some pre-date ritual suggestions:

- What are you going to wear?

- What types of dates feel most comfortable? Is it dinner? Is it an activity? Etc.

- Breathwork or meditation 

- Setting an intention: this is different than a goal, it's more a North Star to guide your experience without putting pressure of hitting certain marks. ex) have a fun experience

Also, REHEARSING your own answers to key questions and figuring out how you like to tell these stories so that when you have to reciprocate, it's not scary. 

4) Not knowing what makes a question good within a dating context: 

Besides genuine curiosity, a good question is one that is:

SPECIFIC & OPEN-ENDED

The specificity is more to contain the scope of the question. "what your philosophy on life?" requires a lot of brain calories and does NOT set people up for success due to it being so unclear what you even mean by that.

This question is likely to make someone feel stupid unless they have thought about it extensively, and therefore, they likely feel like they won't do a great job answering. A better question is something like "if you had to give this chapter of your life a title, what would you call it and why?"

The specificity of THIS chapter in your life creates the parameters. The open-endedness of it is clear as if you asked 100 people this same question, they'd all have unique answers, which makes it a very interesting question. 

5) Not knowing why they're asking the question

This is a topic I do not see addressed often but it is a huge problem and big factor in why I believe many conversations lead to nowhere (in dating and beyond). People often ask questions but if you ask them WHY they are asking the question, they are stumped. 

As obvious as this feels to me now, it was not always at all, I had to train myself to speak with intention. It took some time but now you will not find me asking someone a question without having a reason to ask, even if the reason is sheer curiosity it is a reason. 

This is a VERY common question I get as a dating coach. I’ve thought about this topic extensively and typically it is the result of 1 of these 5 reasons:

It’s very hard to ask someone interesting questions when you’re not particularly interested in them (beyond, perhaps, being physically attractive). Asking someone what their family is like, for instance, isn't a "bad" question, in itself but it also might not be authentic as far as what you 

care about. (See point 5 as well as there may be overlap).

: Be honest with yourself about what you actually like (or dislike) about the people you've been on dates with. If you discover they don’t generate curiosity, then consider exploring why, and also, raising your standards to becoming  more selective with who you go out with.

This may mean less potential dates, so there can sometimes be a self-worth piece to explore here (different rabbit hole). In these cases, more is not more. 

2) Fear of going “off script” and asking bolder, deeper, questions:

 If you are a super beginner and  want some help with this, I STRONGLY recommend you buy this game to play with your next date: 

https://www.werenotreallystrangers.com/collections/games/products/not-really-strangers-card-deck

Sometimes we mistake questions for the source of the problem when really it's a symptom of anxiety and wanting to be liked by your date. 

This is another topic I can expand on upon request. The short answer is creating a ritual that sets yourself up for success on a date SO THAT you go into it having made as many decisions as possible, which eliminates anxiety (something that only exists in the future). 

- What types of dates feel most comfortable? Is it dinner? Is it an activity? Etc.

- Setting an intention: this is different than a goal, it's more a North Star to guide your experience without putting pressure of hitting certain marks. ex) have a fun experience

Also, REHEARSING your own answers to key questions and figuring out how you like to tell these stories so that when you have to reciprocate, it's not scary. 

4) Not knowing what makes a question good within a dating context: 

Besides genuine curiosity, a good question is one that is:

The specificity is more to contain the scope of the question. "what your philosophy on life?" requires a lot of brain calories and does NOT set people up for success due to it being so unclear what you even mean by that.

This question is likely to make someone feel stupid unless they have thought about it extensively, and therefore, they likely feel like they won't do a great job answering. A better question is something like "if you had to give this chapter of your life a title, what would you call it and why?"

The specificity of THIS chapter in your life creates the parameters. The open-endedness of it is clear as if you asked 100 people this same question, they'd all have unique answers, 

which makes it a very interesting question. 

5) Not knowing why they're asking the question

This is a topic I do not see addressed often but it is a huge problem and big factor in why I believe many conversations lead to nowhere (in dating and beyond). People often ask questions but if you ask them WHY they are asking the question, they are stumped. 

As obvious as this feels to me now, it was not always at all, I had to train myself to speak with intention. It took some time but now you will not find me asking someone a question without having a reason to ask, 

even if the reason is sheer curiosity it is a reason. 

I noticed that when I’m a date I have trouble asking good questions of my date. I end up asking dumb questions like “how’s your job? What’s your family like? What are your hobbies?” so boring. Your profile says you are expert on stuff like that. I once had a date with a woman who asked me great questions but I don’t remember what they were. She didn’t go past the first date.

Tessa Mac

How can I ask better questions on a date?