How to Never Run Out of Things to Say On a Date So The Conversation Keeps Flowing Easily post image

You’re on a date, everything is going great, but then the conversation just stops and an awkward silence ensues. One of you sheepishly says: “So, anyway…” but you’re just kind of stuck and a painful silence lingers in the air.

You may get inundated with the following questions, either on the date or after:

Should I have said something different?”

“I wonder what he thought about the story I told.”

“I have to keep talking he’s being so quiet this is horrible.”

“What if I made him uncomfortable when I said I don’t like XYZ?”

“What if I scared him away because of that awkward pause?”

“Wait, is it bad if I text him? Was I boring? Did he think I was funny and exciting?”

“Oh man, this is not good. This conversation is actually painfully boring and impossible to continue.”

This is a common experience. Awkward silences can be brutal. We’ve all dealt with an anxiety-inducing awkward silence at one point in our lives. Even worse, they seem to happen more with people we just meet and more so with someone we want to make a good impression on.

MORE:  225 Amazing Questions to Ask a Guy

Don’t worry… I’m giving you specific strategies you can use so that you never have to worry about running out of things to say on a date.

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Cute Questions To Ask Your Boyfriend (Sweet Things To Ask Your BF) post image

Looking for the perfect cute things to say to your boyfriend? Here’s the best list of questions you can ask your bf to melt his heart!

What’s in a question?

A lot actually! The right questions can really help you get to know someone in a fun, invigorating way. It can take your conversations to a new level and breathe new life into your relationship by giving you something else to talk about aside from how your day was.

We have all sorts of great questions articles on ANM, and this time we’re focusing on couples and cute questions to ask your guy enhance those lovey feelings that make everything worth it.

MORE: 225+ Amazing Questions to Ask a Guy: The Ultimate List

And with that, here is our list of the best “cute” questions to ask your boyfriend.

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355 Good Questions to Ask Someone post image

The Best Questions to Ask People (Whether it’s Someone You Like, People You Know, or Even Your Boyfriend)

Asking the right questions is what opens the gates for a deeper, more meaningful connection. It can deepen a bond with someone you’re romantically involved with, or help you break past those walls we all keep up with a guy you’ve just started dating. The right questions can also help you connect even further with friends and family not to mention, yourself!

MORE: The Ultimate List of Questions to Ask a Guy

You may not even immediately know the answers to some of these questions so you can use them to get to know yourself even more.

Below is my ultimate list of good questions to ask which can be used to start a conversation, pass the time, or make a date more interesting by giving you something more interesting to talk about aside from where you’re from and what you do for a living.

I’ve divided them up to cover a bunch of ground: fun questions, funny questions, creative questions, and interesting questions.

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Good Random Questions To Ask a Guy: The Best, Most Interesting List! post image

The Very Best List of Really Random Questions to Ask a Guy

A lot of people get stuck when it comes to face-t0-face conversations .., maybe it’s because it’s not what we’re used to and it just seems way more intimidating than talking through a screen.

MORE:225+ Amazing Questions to Ask a Guy

Asking the right questions can open the gates for deeper communication and help you really get to know the other person. We usually categorize our question articles but the following list is pretty random. These unconventional questions are pretty out of the box but can lead to interesting answers … which can lead to interesting conversations.

Try them out with a boyfriend, crush or a guy you’d like to be dating.

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The Best Deep Questions To Ask a Guy (Or a Boyfriend Or Man You Like) post image

Use These Deep Questions (To Ask a Guy) and Watch Him Get Serious and Personal With You!

If you’re looking for fun, lighthearted conversation topics well … you came to the wrong place. (Go here if you want fun questions to ask.)

If you want to get to know someone on a deep, profound level, then we’ve got exactly what you need.

Most people shy away from the deep stuff and as a result, most connections are surface level and superficial at best. The way to really connect and get to know someone is to go deep.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

These questions range from personal to philosophical. Some may bring up painful memories, others are mind-benders that are just interesting to think about.

Just know your audience. If it’s a guy you have a crush on that you don’t know so well, you may want to go with some of the more neutral questions. If it’s someone you connect with deeply, then these questions can help you take it to the next level.

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50 Personal Questions to Ask a Guy (That Really Open Him Up!) post image

In the age of texting as a main mode of communication and using emojis and memes to express how we feel, it’s getting harder to build a deep connection. A lot of us are afraid of vulnerability and there are certain places we just won’t go … and few realize that this is the reason so many people have a hard time building genuine connections.

Asking the right questions can push past someone’s walls and get them to open up. You can learn a lot about one another and really form a deep bond and really get to know someone.

MORE: 225 Questions to Ask a Guy- The Ultimate List 

The following list includes all types of personal questions. Some are fairly mild and others really get in there. Pick and choose what you feel comfortable with, and what you think your guy will be comfortable with. The most important rule is to not push too hard. Know when to back off and let it go when he doesn’t feel comfortable answering something, even if you might really, really want to know the answer.

And with that, here are 50 personal questions to ask a guy to get him to open up:

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Funny Questions to Ask (That Make You Look Charming and Hilarious) post image

Everyone loves to laugh, that’s just a given. Humor is a great way to connect with anyone- from a guy you’re seeing to a friend to an employer. It is one of the best ways to bond and just let loose and have some fun.

Being funny comes easily to some people, and is not as easy for others. And everyone has a different scene of humor. Some people are silly, some are raw, some have a dry sense of humor, some have a perverted sense of humor, different strokes!

You don’t need to be a natural comedian to be funny. Sometimes asking the right questions can lead to some belly-aching laughter.

MORE: The Ultimate List of Questions to Ask a Guy to Get Closer

To help you connect with a guy, or anyone really, using a little laughter, we came up with a list of the best funny questions to ask. They’re pretty universal, but you should also use your judgment and tweak as needed based on your relationship and the person’s sense of humor.

These questions are open-ended enough to spark some great conversation. You can either slip these questions into a conversation or tell him you found an awesome list of funny questions to ask someone online and why don’t you give it a try?
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230 Questions to Get to Know Someone: Most Effective Questions to Ask post image

Getting to know someone in this day and age of hiding behind out screens can pose a unique challenge. In many ways, the art of conversation seems to be dying, and the sad consequence of that is people are feeling more isolated and disconnected than ever before.

Whether it’s a guy you like, a guy you’re dating, co-workers, or your friends — how much depth of connection exists in your relationships? How well do you really know the people in your life, including those closest to you?

A lot of people feel awkward or nervous in conversations, especially a conversation with someone they’re trying to impress. You end up talking about nonsense and no real connection is formed.

And here is what most people forget. Conversations aren’t meant to impress someone, they are meant to discover someone

MORE: 225+ Amazing Questions to Ask a Guy

You don’t need to do tricks or play games to make him like you, you just look at what’s there and take it for what it is, and you let things unfold naturally without force or agenda. When you can do this, it totally takes the pressure of you and you don’t have to worry about “failing” with a guy, or being rejected. You are just talking and discovering what another and seeing if it’s a good fit (this also applies for networking and job interviews).

Now that you have the right mindset, let’s look at some specific things to say so you can be a master conversationalist and actually form real connections and get to know people on a deeper level.
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