17 Revealing Questions to Ask a Guy During Your First Month of Dating

17 Revealing Questions to Ask a Guy During Your First Month of Dating

Posted by in Black Love Advice

“I’m in a new relationship.” Those words can be exciting and daunting at the same time. It’s natural to be excited about your new relationship.

It’s also normal to want everything to go perfectly.

One of the most nerve-wracking things in a new relationship is determining how compatible you are.

The difficulty of this mainly stems from our inability to see our partners flaws during the emotionally charged honeymoon phase we all experience during the first few months of dating.

Well, these questions to ask a guy during the first month of dating can definitely help you see through the initial blindness your new relationship might be causing.

These questions are designed to help you figure out if you want to invest more time in the relationship, or even if you want to take the relationship to the next level.

Here are 17 good questions to ask a guy in your first month of dating…

1. What did you do on your last vacation?

This can tell you a lot about a guy’s priorities.

Did he spend it with friends hanging out at bars? Did he travel? Did he spend his time working on a side business he’s building?

This question can also give you some serious insights into how your man likes to spend his free time.

If you continue in this relationship, chances are, how he spends his free time will become an issue if you don’t like it

2. Do you have brothers and sisters?

This question isn’t too forward or unexpected.

It’s a common question to ask on a first, second or third date.

It can tell you a lot though.

If he enthusiastically launches into details about his brothers, sisters, and cousin’s, you can expect family to be a big presence in his life.

On the other hand, if he offers vague answers without a lot of details, it might be a sign that there’s some dysfunction in his family.

3. What was the last movie you saw?

17 Revealing Questions to Ask a Guy During the First Month of Dating

Asking questions that have simple answers can be very insightful.

Unless he’s going to lie, he can’t just tell you what he thinks you want to hear. That means you can learn a lot about him this way.

Was his last movie an action flick or a romantic comedy? Was it so long ago he doesn’t even remember?

From there, you can ask him if he liked the movie and what he thinks of certain actors or actresses in the film.

4. What’s your fitness routine?

All men should find time to stay fit.

Does he like to walk or lift weights? Is he more of a basketball or a bike person?

This is a great question to ask because it can help you find things that you like to do together.

Also, if his answer is that he spends all night, every night at the gym, this might not be the type of relationship you’re looking for.

Indeed, dating someone that’s basically addicted to the gym comes with difficulties.

5. What’s your most embarrassing moment?

Ask this question and be prepared to have to answer it yourself.

You might hear a funny answer.

But what you’re really trying to gauge is how he handles himself when things don’t go his way.

6. Do you have a favorite food?

A good icebreaker, this question can set up other date ideas. Maybe you’ll find out that you share a favorite restaurant.

Perhaps you can cook him a dish that he likes.

This question opens up a lot of possibilities.

7. What apps do you have on your phones home screen?

What a person chooses to do with that limited phone space can be very telling.

Does his most used apps help him play online poker or learn a foreign language? Do they help him manage his finances or communicate with friends and family?

As inconsequential as this may seem, there might be some signs there that he’s a great guy to snatch up or there might be some warning signs.

8. Who do you live with?

This is a practical question as much as an insightful one because you don’t want to show up at his place and find any surprises.

This is also a great way to learn more about your man’s personal background and how he got where he is today.

9. Do you follow any college or professional sports teams?

17 Revealing Questions to Ask a Guy During the First Month of Dating

If he says yes, this can branch off into other talking points.

You can talk about your favorite teams and who deserves to be in the all-star game.

Most men love sports and take it very seriously, so this is a great question to get him to open up.

10. Have you been out of the country?

With this question you can learn about where your guy has been, and why.

Does he take trips for work? Does he have family living overseas that he goes to visit?

Is he an adventurer with a taste for the unknown?

This question can uncover a lot about how your time together will likely be spent in the future.

11. Are you religious?

This is a big question, maybe even the BIGGEST.

And he should have a definitive answer.

If he’s devout, he should be proud of it. If he’s not religious, he shouldn’t hide that fact either.

Ultimately, you need compatibility on this issue or it’s likely going to cause problems in your relationship in the future.

There’s no sense in beating around the bush here.

12. Who is your biggest role model?

Of all of the questions to ask a guy, this might be the one that tells you the most about his values.

If he says his role model is Birdman or Al Capone you should probably think twice about pursuing a serious relationship with him lol.

On the other hand, if he says a family member, a businessman, or someone that’s honorable and at the top of their professional field, he’s probably got his priorities in the right place.

13. How long ago was your last relationship?

Nobody likes to be a rebound.

You can use this question to make sure you aren’t one.

The man you’re dating should have more than a one-word answer for this question, too.

He should also have some insight into what happened and why it didn’t work out.

14. Do you like to dance/fish/travel/play with dogs?

Whatever your absolutes are, now is as good of time as any to start poking around for answers.

If you can’t live without dancing, make sure your guy isn’t too shy to take to the dance floor.

When you absolutely can’t live without traveling, make sure your man is going to go along for the ride.

Clearing up these little things now can help you have a clearer picture of your future together.

15. What’s your favorite day of the week?

This is another good question to start a conversation.

It can lead to clues about how he relaxes and what stresses him.

Does he like a lazy Sunday or an adventurous Saturday? Does he live for the thrill of Monday’s team meeting at work or his Wednesday night softball league?

The answers might surprise you.

16. Which chore do you hate the most?

It’s a funny thing to talk about, but it’s also a fun way to talk about daily life.

Sometimes, in a relationship, the person who ends up doing a chore is the person who hates it the least.

So you definitely want to make sure you see eye to eye here.

17. What’s your favorite snack?

If you need an idea for a birthday or holiday gift early on in your relationship, a basket of his favorite goodies can be a winner.

This question is a good way to start gathering ideas on the sly.


Starting a new relationship can be fun and exciting. However, at some point, you have to start actually gauging your level of compatibility beyond the initial attraction.

These 17 questions to ask a guy are an excellent starting point. And asking them won’t seem awkward at all so ask away!

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