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 exhibit 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 a knowledge 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.
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 an Ex
Obviously, you’re going to be extremely excited to get another chance with your ex if it’s someone that you have missed and regretted losing. But before we get into what you should say when the first date with someone you already know happens to be an ex-girlfriend, let’s take a look at whether or not it is actually a GOOD idea for you to be revisiting a past relationship — after all, you guys did break up for a reason.
It’s a Good Idea If…
- You were able to successfully get over and heal from the breakup, and move forward with your life
- Both of you have agreed to the date and are eager to see each other again
- Both of you are currently available
- You learned from the relationship and things that were issues in the relationship before are not likely to be a big deal now
It’s a Bad Idea If…
- You never moved on and the things that happened during your relationship still cause you to feel hurt, sad, and angry
- One or both of you are in relationships or rebounding from a relationship
- You’re returning to your ex because you feel like there are no other options
Now that we have that covered, let’s break down some things you should talk about.
How Well You’re Doing Now
Even the hardest breakups come with benefits. Relationships give us the opportunity to grow and practice self-reflection. Think about what the issues were that caused your ex to decide she didn’t want to continue a committed relationship with you. Was jealousy an issue? Were you financially or emotionally dependent on her? Did she think you lacked motivation?
Without specifically bringing up the breakup, show her through your words and actions that you have changed for the better. Talk about the experiences you’ve had and how you’ve grown.
Ask Her About Things You Know Are Important to Her
This date is not about dwelling on the pain and hurt of the past. Part of this date should be a celebration of how both of you have grown and changed for the better.
Think about the things that were important to your ex and ask her about what’s been happening with things like her job, her friends, her family, her cats, etc. etc. etc. Applaud any achievements she’s made.
I’m sure that you’re nervous going on this date and that is COMPLETELY understandable. Going on a date with anyone can cause some anxiety; dating someone who left you adds an extra level of vulnerability.
But remember that you’ve been here before. You got this person to commit to you and, despite breaking up, she saw several things in you that made her decide you two had a potential future together. You can recreate that chemistry and connection. And, if things go well, you could end up back with your ex in a relationship that is stronger and healthier than before.
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 comes to going on a first date with someone you already know, everyone’s situation is unique. I’d love to learn more about your specific situation so that I can help you knock this first date out of the park and be on your way to an exciting new relationship.
Check out my calendar and book a new client session with me today. During our initial session, I’ll provide you with expert strategies that will help you to address your dating roadblocks, create dating goals, and create an action plan that will keep you out of the friend zone. We’ll also determine if my 3 month coaching program (Signature program) could help you reach your dating goals even faster!