Late Night Conversations With Your Crush: A Complete Guide
We have all been there, staring at your phone and having late night conversations with your crush. It is easy to let the time slip by and become infatuated with the conversation.
When we first started dating, we had plenty of late night conversations that kept us up till god knows what time in the morning. Not only did this make us feel closer, but it also allowed us to have a consistent stream of conversation that is sometimes hard to do during the day.
It is so normal to get nervous when speaking to your crush. Therefore we have come up with our top 10 late night conversations with your crush. It is also hard sometimes to think of new things to talk about with the person you like.
Check out the book “How to Talk to Anyone” to learn the 92 little tricks we’ve applied to our relationship.
What Makes A Good Late Night Conversation?
Now, this is really a personal opinion. Everyone is different and will have a different idea of what makes a good late night conversation. Therefore, we will try and make this as broad as possible.
In our eyes, a late-night conversation makes you want to stay up all night talking to your crush. One that makes you not want to put the phone down and leaves you with a big smile on your face.
A late night conversation with your crush can also leave you feeling closer to them due to bonding over shared interests. It could be light-hearted topics such as favourite music to deep conversations like questions about family.
If you want to measure what makes a good late night conversation, it could be the topic you talk about. If you get deep, it could help you deeper on an emotional level. Or, it could have resulted in a date or planned trip which makes you feel hopeful for the future.
Some might measure a conversation as good if it made them laugh. Laughter when you are getting to know someone is great. Don't get us wrong; we love a deep conversation, but you have to be able to laugh and joke around together.
Don't get too stressed about what makes a 'good' late night conversation with your crush, as there isn't a right or wrong answer. The most important thing is that you feel happy and comfortable with the conversation.
Top 10 Late Night Conversations With Your Crush
What's Your Crush's favourite thing about themselves?
Things can get deep quickly when having a late night conversation with your crush. It makes sense. You are lying in bed, all cosy with nothing else to concentrate on but each other.
This leads nicely to you starting a conversation about your crush's favourite thing about themselves. What we love about this question is it's not something that anyone will get asked often. Therefore, it requires your crush to think about the answer.
It can then spiral into several conversations as you start to dive into the depths of each other's personalities. It also gives you a good indication of their character based on their answer, whether they are confident and say their looks or body. Or whether they are a bit more introverted and say attributes like kind.
It is also good to keep note of these for the future so you can complement them when they are down.
What is something your parents would be surprised to know?
This is an entertaining topic of conversation to have with your crush at night, as the answer could literally be anything. If it is something their parents don't know, it is bound to be juicy!
It is also a great excuse to start a conversation with your crush because it will definitely get them interested. It could be when you snuck out of the house or pretended to stay at a friend's when you really went to a party!
Sharing secrets can bond you as a couple as you learn things about each other that no one else knows.
What is your worst pet peeve?
Late night conversations don't need to be deep; they can be light-hearted and fun. Learning your crush's pet peeve is good to get out of the way early on. This way, you can see if their pet peeve is something you do!
It can also be something you bond over if you have a similar pet peeve and similar reasons for it. For example, Henry and I dislike people who don't have manners. We bonded over this on our first date, and both said it was a turn-off if someone was rude.
Nothing is worse than someone grinding your gears, so it is good to be aware of these things from the beginning. It can also be used to flirt in the future by teasing them now you know their weakness!
If your crush has one of your pet peeves, you may struggle to talk to them. Try “How to Talk to Anyone About Anything” to get over this.
What is your biggest turn-off?
Talking of turn-offs, this could also be a great late night conversation with your crush.
Another word for turn-off these days is an ick. This can be anything that is a big no-no and instantly puts you off someone. I am sure you have plenty, so it is a good chance to see if your crush has any of yours.
When we first started dating, I explained icks to Henry, and luckily it did not put us off each other. However, it is a great way to ensure you don't fall into any of your crush's turn-offs. If you do, you'll know what not to do on the date!
What did you think when you first met me?
This is a really juicy one and not for the faint-hearted. Finding out your crush's first impression of you is a bold step and can really change the whole dynamic.
Whether you have not met yet or just started dating, figuring out first impressions can be intriguing. It might be really good and strengthen your bond, or it might show your crush's true colours and save you a lot of time and effort.
Either outcome, in our opinion, is good as you are putting yourself first. First impressions are important and give you a good indicator of how you come across. Be brave; you never know what the answer could lead to!
If you could go anywhere in the world, where would it be?
This is still a late night conversation that we have to this day. We are biased because we love to travel, which was a big thing we bonded over. Hence why we started A Couple Things To Do to document our travels.
Asking your crush if they could go anywhere in the world where it would be is a great late night conversation as you can get imaginative. Then, at night, you can let your imagination run away with you and bond over similar dreams.
This can really tell you whether your crush has the same desires and aspirations as you. Now, it might not be that deep yet, but if you love to travel and your crush doesn't, then it could be a deal breaker.
Who knows you best?
Figuring out who knows your crush best is something that will help you in the future. Creeping it into a late night conversation with your crush is a great way to do this.
This gives you an insight into who they are close with and who they hang out with. It also lets you know whether they are a family person or not. If you are family orientated and it is an important quality for you, someone that is not might not be a good match.
Say that their best friend is the one that knows them best; you can remember that for the future and ask them questions when you meet them. It also lets you know whose good books you need to be in!
What is your biggest accomplishment?
This is a question I asked Henry that helped him come out of his shell and helped us bond. As Henry is a very accomplished person, this is somewhere he thrived and therefore made me more attracted to him.
A big tip when trying to find a late night conversation topic is that people love to talk about themselves. It is human instinct to talk about yourself because it is all you know. Therefore, asking about your crush's most significant accomplishment could lead to a whole host of conversations.
It also makes you more attracted to the person as watching someone talk about what they are proud of makes them even more attractive. We found that we had many similar goals and achievements in life, which automatically brought us closer.
The most important question: What is your favourite food?
Not everyone will think this is important. But as a couple, we absolutely love food! We bonded over our shared love for Asian food, which has led to us trying so many Asian-inspired restaurants.
This is a great light-hearted topic for a late night conversation with your crush. Talking about what food you like is a fail-safe topic as everyone has a favourite food. You can even introduce some flirting here as you mock the other person's food choice.
It is also an excellent opportunity to smoothly ask your crush on a date. If you are already on the topic of food, you are halfway to asking them out. It also makes your job easier as they now know your favourite food!
Talking about a common topic can help each other feel more comfortable and highlight things you might have in common. Or it will let you know whether your crush's food tastes the opposite of yours!
What is one thing in the world that people love but you think is overrated?
We have spoken about serious and light-weighted late night conversations with your crush, so we thought we would throw in a controversial one. When we first started talking, I would say controversial topics were something we liked to touch on often.
Therefore, asking your crush to pick one thing in the world that people love but they think it is controversial is going to be super interesting. It could be something you love that will never end well.
It helps you to see if your crush has any controversial political views or views on religion that don't align with or even an opposing football team. It can open a can of worms. This is needed, though, to test your crush against your criteria thoroughly.
Late night conversations with your crush: Conversations starters
So now we have given you ten late night conversations with your crush; let's look at some flirty text conversation starters.
It is all good and well, having plenty of topics to discuss, but it might not be as effective if you don't have a smooth way to approach it. Therefore, we are here to give you the full package and help you as much as possible.
Flirty late night conversation starters
"I am supposed to be sleeping right now, but I can't stop thinking about you." - If you received that message, it would be hard not to make you smile. It shows your crush that you are thinking about them so much it is stopping you from sleeping. If they reply, it is the perfect gateway to a late-night conversation with your crush.
"I was going to play it cool tonight and wait to message you, but I couldn't wait that long to talk." - If this doesn't show your crush you are interested, then I don't know what will. Showing you are excited to talk to them will make it clear that you are into them. It will allow you to lead nicely into a late night convo.
Let's be honest, flirty conversation starters can go one way or the other - either you'll end up on a perfect date or it'll be the last time you end up texting your crush. Sometimes it's just best to wait a day or two to text if you're unsure.
Deep topics late night conversation starters
"Tell me the best thing that happened to you this week." - Not only is this a thoughtful message, but it can also lead to a deep conversation. Discussing the highs from your week can allow you to lead on to deep topics by bouncing off their answers.
"If you could be anyone for one day, who would it be and why?" - Similar to some of our topics to talk about with your crush, this is a great gateway conversation starter. It is light-hearted as you can have some fun with it. But then you can lead into some deeper questions after.
Late night conversations starters that will lead to a date
"I'll be able to sleep better knowing I'm seeing you soon. Are you free this weekend by any chance?" - Super cheeky but super fun! You can't help but smile when you see that message. It lets your crush know they are on your mind and that you want to solidify a time to see them. It is also forward and directed, showing confidence which is always attractive!
"Now that I know your favourite food is Pizza, do you fancy trying out the new Italian restaurant in town this weekend? - Leading on from one of the late night conversation topics we mentioned earlier, using this to initiate a date is smooth. As you are already on the topic of food, why not shoot your shot and ask them on a date? Even better now you know their favourite food!
Conclusion: Top 10 Late Night Conversations With Your Crush
We hope this blog has given you plenty of new ideas for having a successful late night conversation with your crush.
However, as we always say, the best thing you can do is just be yourself and don't overthink it. Don't be too strict with yourself, feeling as if you need to follow this step by step, do whatever comes naturally to you.
This blog is purely to give you some ideas when you are stuck on how to start a late night conversation with your crush and what to talk about. We know it can be nerve-wracking, and sometimes your brain goes blank!
If you like this blog and want us to do more like this in the future, then do get in touch!
