Becoming romantically involved with someone who was once a friend can have its own unique set of benefits and downsides within the relationship. Dating someone who was a friend initially is how many people go on to form romantic relationships. You create that special bond with someone which ultimately leads its way on to more. It may be sort of a surprise that it happened, or it could be something you were secretly hoping for! Either way it can feel nerve wracking to make the transition, especially when you think about going on that first “date.” Here are some things you can talk about to help you prepare and guide conversation, as well as some things you should stay away from!

First things first 

Since you already know the person, there’s no need to go over all the basic stuff. Instead, you should focus on why you are going on the date in the first place and what you are trying to achieve from it. This isn’t meant to rush you, rather just get you thinking about the point of getting out there and going on the first date. You can ask them more specific questions like what their dream job would be or where they want to live someday, to see if both of your paths and goals will line up the same over time. Prior to the date, think of questions you might want to ask or segment into a way about where you guys might end up together. Maybe you’re ok with casual dating at the moment and going from there, or you might be trying to just settle down already. What points in life are you both in? Have you guys had feelings for each other for a while? Lay it all out there on the table. Let yourself observe the romantic chemistry and see how it feels to you. 

How do I know if there’s chemistry with someone?:

  • You feel like your authentic self when you’re with the person.
  • You enjoy the time you spend together. 
  • You notice small, maybe quirky details about their personality and character. 
  • Physically you feel very comfortable and safe with the person. 
Friends playing pool ball
We can find chemistry between others in shared activities or hobbies.

Make an effort to learn new things

I’m sure you already know many details of your date’s life and who they are. But once you become romantically involved, the connection only gets deeper. Make the effort to ask questions to try and learn some new things about the person. These questions can also be romantically involved of course!.

Here are some ideas regarding questions you can bring up to learn more about them:

  • What motivates you to work hard?
  • What is your proudest accomplishment?
  • What are your pet peeves?
  • What’s your favorite family tradition?

You can even ask them if they have a hidden secret talent or two! Regardless, you should make an effort to learn some new things about your friend. This will show interest and help you to understand more about the date to decide if they are a good match for you! 

Use the past as a benefit 

Like we’ve mentioned previously, when going on a first date with a friend there are going to be a lot of things you know about them already. If there are moments throughout the date where you don’t know what to talk about, or feel there is too much awkward silence, you can use the friendship as a benefit. Talk about inside jokes or fun memories you may have had in the past. If you have mutual friends, you can also take some time to talk about them a little bit! 

Couple enjoying coffee together
Sharing jokes is always a great way to build connections with people and ease some tension.

Impress them 

Friendship presents itself with a level of familiarity. Think of ways you can do something special to stand out this time and impress your date. Maybe you’ll want to dress up in something you’ve never worn before to show off, or reveal an accomplishment about yourself they never knew. Either way, take this opportunity to stand out and grab their attention! 

Some other words of wisdom 

There are some things you should expect to happen when transitioning from friends to lovers. That friend status will change, which may bring on some upsets. True friends are always there for you when you need to vent and let it out. When you start dating a friend and issues arise, you’re not going to be able to vent to them the same way you did previously. Because this time the issue could be from that former friend who you’re dating now! Communication in a relationship differs from communication in a friendship. We tell our friends everything and can fully let loose around them, while a relationship can often function differently and we are not as open with everything. 

Don’t rush things 

Even though it is appropriate to ask questions about the date’s future and what they would want out of life in general, it’s important to remember to not rush the process. It’s okay to be curious about things such as their place in life and where they want to be someday, but avoid taking any actual big steps towards the romantic relationship right off the bat. During the date, please just remember to have fun and enjoy yourself first. You can remain casual in conversation, and don’t feel like you have to go over everything the very first time. Take things step by step!

Physical intimacy is a topic that differs from person to person. However, it’s important to note that too much touching and a sexual relationship formed right off the bat can confuse the meaning of the relationship and conflict with boundaries. If you act on sexual urges too soon, this can lead to things feeling more awkward after the fact and you might lose that innocent romantic connection you both were starting to share with each other. 

Early sex can create something known as counterfeit intimacy. This happens when both partners think they are a lot closer to each other than they actually are, and can even get themselves convinced that they are both “in love.” All in all, you know yourself more than anyone else. Make the right choices you know you won’t regret later on! 

Partners hugging each other
A hug is the perfect first physical connection to share!

Avoid assumptions

Because you were already friends prior to going on the date, you might think you know some details about what the other person wants out of a relationship. Or, you might have been told information previously that doesn’t apply to the current situation.

Here are some examples:

  • Maybe your date told you they didn’t want a codependent relationship in the past. Don’t assume they automatically want you to be distant. Once you build more of a connection, you will discover how they function in a relationship. 
  • If you knew about their previous romantic partners, avoid assuming how their relationship dynamics are right off the bat. We can act differently around different people!
  • Don’t connect all of their behaviors as a friend to how they will act as a romantic partner. Two completely different situations!


The transition from friends to romantic companions presents itself with some risks. If the relationship doesn’t work out, there’s a good chance you won’t be able to return to that same friendship you two once had. This can be from a mixture of hurt feelings and even jealousy regarding the past relationship. Even if there were issues to arise that just concerned the two of you, these problems can spread and make their way on to other mutual friends. Sometimes when someone decides to date a friend and it goes haywire, mutual friends of both parties can take sides. 

So when you decide to start a relationship with a former friend, understand that there can be potential threats to other friendships in your life as well. However, if you feel like the romantic dating route is the way to go with your once friend, always do what’s best for you. Just remember to create a mindset that the romance might not completely work out. 

If you are reading this and happen to be going on your very first date with a friend soon, good luck! Remember to use this opportunity to learn more about the date both as a person and potential romantic partner, and avoid moving too quickly.

Jul 22, 2022