No matter how far back you go with someone, it can be intimidating to think about what to talk about on a date if you already know the person. Because you have at least a basic knowledge of each other, certain first date questions won’t make sense on this sort of date.

Regardless of how you know the person, it’s important to keep in mind that some standard first date rules will still apply:

• Make sure you pick her up, pull the chair out for her, pay, and show other forms of chivalry
• Show initiative and intent by securing a time, date, and location (what we refer to as TDL) for this date, as well as the second and third date

Without further adieu, take a look below for my professional tips on what to talk about on a date if you already know the person, whether it’s a coworker a friend or even an ex.

And because everyone’s situation is unique, I am including some information at the end of the article on how you can connect with me to have the most success on your date.

When It’s Your First Date With a Coworker

First things first — DON’T get bogged down in work talk and venting about work. Take this opportunity to get to know your colleague’s interests and personality outside of the confines of the office. Some important things to keep in mind in this particular situation are:

Keeping it Light

Maybe you and your coworker have been attracted to each other for a long time, but you were worried about crossing a boundary. Wanting to get to know someone romantically who is off limits can stoke the sexual tension and leave you feeling exhilarated when you FINALLY get to go on a first date with them.

That being said, remember that you actually don’t really know this person outside of work, and the fact that they were forbidden fruit could have actually made you idealize what they’d be like as a girlfriend. And she might have idealized you in the same way.

As exciting as the first date might be for both of you, remember that the reason for you not initially going out is something rather common — work. It’s not like your families are the Capulets and the Montagues.

Maybe you two will end up together forever, or maybe you’ll discover that you’re not as compatible as you once thought.

Regardless, it’s in your best interest to keep the conversation light. Ask about her interests outside of work, what she was like growing up, etc.

Using What You Already Know

One of the advantages of going on a date with someone you already know is that you’re coming into the situation equipped with information you wouldn’t have otherwise. If you’ve chatted about shared musical interests, for example, you can talk about plans to see one of your favorite bands or a concert that you think she would like.

What To Talk About When She’s A Friend Of A Friend

If you’re on a date with a friend of a friend, first of all you should be profusely thanking the friend that set you up.

Not only because they set you up with a cutey, but because they will now be the basis of your conversation.

I’m not saying you need to talk about Steve for the entire first date – she might get the wrong idea. But use Steve as a starting point.

Ask her how she knows Steve, chat about your relationships with him, and naturally grow the conversation from there.

Some questions you might ask are:

Other Passions

One thing that can create attraction between coworkers is a shared passion for your chosen vocation. Although it’s best to steer clear of conversation that relates to where you both work, there’s nothing wrong with learning more about her career passions outside of her current job.

You can also use the opportunity to find out what led her to the company you both work at now, as well as where she pictures herself working if she doesn’t intend to stay at the job for a long time.

Dating a coworker can be tricky business. If you’re finding yourself interested in someone you work with, click here to learn more about the rules that come with dating a colleague.

When It’s Your First Date With a Friend

Welcome to the first step out of the friend zone! Woohoo!

When you’re going on a first date with someone you already know, and that someone happens to be a friend (not an ex, not a co-worker, not an acquaintance, but a friend) you’re already set up for success.

Good friendships come with a foundation of compassion, trust, and respect. Those three elements are also integral to a successful romantic relationship.

Because you two already have a great time hanging out as friends, it shouldn’t be difficult getting the conversation to flow. If your friend has agreed to go on a date with you (or even been the one to ask you out), it’s because she’s already hip to the fact that you are one awesome guy. For that reason, it’s really important that you be yourself during the date and act as normal as possible.

Still, women love mystery, so don’t go on the date without showing you have a few tricks up your sleeve. Reveal something about yourself that she doesn’t know already know. Show her your more sensitive, romantic side and don’t shy away from turning up the heat.

Break the touch barrier between you two but resting your hand on a non-threatening area (a shoulder, knee or her forearm) during the conversation. Do all the things you would normally do to show your chivalry during a date, such as picking her up, paying and walking her to her door. If things go well and the chemistry you anticipated is there, chances are good that this lucky lady could go from being your friend to your girlfriend.

When It’s Your First Date After A Break

Obviously, you’re going to be extremely excited to date your former partner after a break. It feels like the very first time you two have gone out as you’re both recharged and are looking at this relationship through a new lens.

Chances are if you’re now done with your break and dating again, you two have already had in-depth conversations about how you feel about each other, the future, why the break too place, etc.

There is no reason to re-hash these things – especially when you’re on a date!

To make sure things go smoothly, I recommend revolving the date around an activity.

Things have the potential to get a little awkward so why not put the spotlight on the activity rather than on yourselves?

That activity could be as simple as going on a hike or bike ride.

Considering this is your second-chance at a relationship you clearly care about I recommend doing something special or at least out of the norm. Think of something your partner is super into and build a date around that. Show her how much she means to you by crafting a super special date.

If she loves tarot cards, go for a reading. Maybe she’s a massive sports fan, so go watch her favorite team live. And if she loves dancing to live music go see a show.

Whatever you do try not to go to just another boring dinner or worse – get coffee.

Plan the date around an activity and you won’t have to worry about what to talk about as the conversation will flow naturally.

The 70-30 Rule

If you want someone to like you, allow them to do most of the talking. This is Dale Carnegie’s advice, the author of the second most popular book behind the Bible, How To Win Friends And Influence People.

Everyone’s favorite subject is themselves, so let them do the talking. Not only this, but we absolutely love when we feel as though someone else genuinely cares about what we have to share and who we are.

By asking probing questions and genuinely caring about the answers (as shown by nonverbal cues and by asking follow-up questions) you can quickly build attraction.

Listen to what she has to say, care, and ask follow-up questions. Doing this may not guarantee a second date but it will certainly endear you to her.

I should also note that questions should arise organically. Randomly asking her a question out of the blue could throw a wrench in an already flowing conversation. Keep things natural, smooth, and free-flowing.

Refine Your In-Person Dating Skills

When it comes to going on a first date with someone you already know, everyone’s situation is unique.

In our coaching program, Dating Decoded we offer modules via our online curriculum that dive deep into how to have amazing first date conversations. We also tackle this subject via our two weekly live coaching sessions. But even though equip you with the skills you need to have amazing first dates you still need a safe place to practice.

That’s where our mock dates come into play.

Practice what you’ve learned in our program withe Audrey or Brooke, our mock date specialists. In-person or online you’ll have a practice date to use and refine the skills learned in our program. After the date you’ll received detailed feedback on what worked and what areas need improvement.

To learn more about our program and how we can help you prepare for your big first date, book a 1-on-1 Zoom call. 

Here we’ll talk about your dating history and dating goals.

And if you’d like to know how our students’ lives have changed after enrolling in Dating Decoded, hear what they have to say here. Or, just check out one of our student’s video reviews here: