What to Talk About on a First Date with Your Best Friend?

Turning a beautiful friendship into something more can be quite exciting, especially if there’s chemistry between you two.

But if you’ve been friends for a long time, it can be hard to figure out what you two can talk about on your first date. There’s no denying that taking your friendship to the next level can be beneficial for you, but it can also be surprisingly awkward at first.

However, if you know just the right questions to ask and use your history to your benefit, you’ll be able to keep the conversation flowing right away and get to know them on a deeper level.

In this blog post, I’ve prepared a few tips and pointers that you should keep in mind when you’re going on a first date with your best friend.

What to Talk About on a First Date with Your Best Friend?

Standard First Date Rules Still Apply

Regardless of how far back you go with your best friend and the life-changing experiences you’ve had together, it can be quite intimidating to think about what to discuss when you already know so much about them. 

No matter what you do on the first date, you should keep in mind that some standard first date rules will still apply. If you’re a guy, you should make it a point to pick your best friend up, open the door for her, and show other forms of chivalry. 

Whether you’re a man or a woman, you need to show intent and initiative by doing something you both have never done together. It’s also advisable that you try to look your best on the first date because attraction holds a lot of importance, especially at the beginning of a new relationship.

1. Be Honest and Upfront about Your Motives

By now, you probably know that communication is incredibly important in relationships that are built out of friendships. Since you’re already compatible with your best friend and easily get along with them, you should strive to keep it that way on the first date. 

Remember to be direct about what you’re looking for so there are no false expectations and everything’s clear from the get-go. Moreover, make sure you’re both making an effort to stay on the same page. 

It’s true that you should go on the first date with excitement, but you shouldn’t forget that it may not be all roses as you may have imagined. Things can easily go south if you aren’t careful with your words and you may realize you’re better off as friends. If staying friends regardless of what happens is important for you, you should make that clear right away. 

2. Use Your History to Your Advantage

Needless to say, the scariest thing about a first date is not knowing anything about the person you’re meeting up with. You go into it knowing little to nothing about what you can expect. But when you’re going on a first date with your best friend, you already have some idea of what may happen, and that can help put you at ease. 

Best of all, there are so many topics for a conversation you can choose from. You can talk to them about old times, the first impression you had of each other, inside jokes, and a lot more. Since you already know the basics about them, you’re more likely to have a meaningful conversation.

If you happen to have similar musical interests, you can talk about future plans to see your favorite band together or get to know more about their other interests to see if you have something else in common that you hadn’t known about before. 

3. Remember to Keep It Lighthearted and Fun

It’s possible that you and your best friend have been attracted to each other for quite some time, but it’s understandable if you’re worried about crossing a boundary and making them uncomfortable. There may be sexual tension between the two of you, but that doesn’t mean you can’t have a lighthearted and fun first date. 

It will serve your best interests to keep the conversation light. You can talk to them about where they grew up, what their family was like growing up, and other questions of the like to get to know them better. 

4. Discuss What Sparked Your Interest

Since this is your first time seeing your best friend in a new light, you shouldn’t forget that you may have idealized what dating them would feel like and they may have idealized you in a similar way. The first few dates are an opportunity for you to figure out if you’re meant to be together or if it’s better for you to stay friends. 

A great way to start the date with your best friend can be to talk more about what sparked your interest to suddenly go in this direction and whether you’ve had feelings for them for a long time and only just decided to pursue something more serious. 

Think about it: discussing what changed things can give you both a glimpse into why you got attracted to your best friend in the first place. This will be something you can hold onto when you move forward. 

5. Don’t Think Too Far Ahead and Enjoy the Moment

Since you’ve been with your best friend for a while and you’ve probably seen what they were like in their past relationships, you may already have preconceived notions about the kind of role they play in most relationships. 

That being said, you shouldn’t let the past affect your judgment because it’s a completely different thing to actually be in a relationship with someone. Instead of thinking too far ahead, you should learn to enjoy the moment and let things fall into place. 

Use the first date as an opportunity to learn about your friend. Think about some topics that may have been off-limits for you before this stage, so you can open up and be more honest about what you want in the long run. 

Tips to Keep in Mind Once You Start Dating Your Best Friend

When you finally start dating your best friend, it’s completely normal to feel overwhelmed and scared at the same time. You already knew this person before dating them and now you get to be more intimate with them, and that can take some getting used to. As thrilling as it might be, dating your friend may not always be as easy and natural as most people would have you believe.

After all, going from best friends to lovers is a huge change. Becoming romantically involved with someone requires effort and intentional thought so you can build a strong connection and make sure it lasts forever. You need to be open to change and embrace the process if you want to have a better chance at making it work. 

Here are some tips I’ve narrowed down that can help your new relationship thrive:

1. Develop a Routine So You Can Settle Into the Relationship

Transitioning into romantic partners requires you to change your schedules and adapt so you can become more available for each other. You may end up spending more time together now that you’re dating, depending on what feels right. 

Get a feel for what it’s like being around and remember to express all your fears and concerns so you can build a healthy relationship based on trust and mutual understanding. Go on date nights on Saturdays, or spend the whole weekend together, it’s up to you. As long as you’re honest with each other and show compassion, you’ll be able to make it work. 

2. Don’t Be Afraid to Get Intimate

Before dating your best friend, you may be used to hanging out with them in groups or casual settings. But now that you’re a couple, that may change drastically. Don’t be afraid to get closer and be affectionate with each other whenever you can. Don’t let the nerves hold you back and let simple and beautiful moments like that come naturally. 

Start slow and be gentle. You can try holding hands and sitting closer together first if it all feels too unfamiliar and new. Small touches and brushes can be quite intimate and may lead to something more. 

3. Don’t Move Too Fast

If it wasn’t obvious, you need to take things slow, especially in the earlier stages when you’re both trying to get comfortable being around each other. When you get too serious too fast, you’ll end up missing out on beautiful moments together. Furthermore, you won’t be able to allow your relationship to fully grow. 

Much like every other relationship, you both need to go through all the different phases so you can emerge even stronger than you had hoped. Remember to take your time so you can build a relationship that you can sustain in the long run. 

Final Thoughts

If you go into it with the purest intentions, dating your best friend can be nothing short of magic. Being able to get intimate with someone you can trust with your secrets and fears is basically like winning the lottery. Remember not to get ahead of yourself and enjoy every moment as it comes so you can allow your relationship to grow into something even more beautiful.