Online Dating Blog

There are times where a first date is going great. The two of you are finding a lot in common. Then you say something to be funny or without much thought and realize you’ve offended your date. Suddenly the mood changes and your odds of a second date go from almost-guaranteed to non-existent. So how do you handle this situation?

First off, in my last article I pointed out that many people are overly-critical of themselves. What I’m talking about in this article isn’t something like forgetting to open her door, showing up to the date two minutes late or even disagreeing on which Star Wars movie was the best.

I’m talking about that moment where you actually feel the air turn cold and see your date turn from someone who is answering questions in a fun way to someone who answers everything with one word and keeps looking at their watch. So if you think you’re always bad on first dates, you probably need to check out the link above instead.

Addressing the Issue as it Arises

If you say something you know your date took offense to, I suggest addressing the issue right there. Don’t let it sit with no comment until you have an elephant in the room and both of you are trying to pretend everything is fine when it is absolutely not.

Now I’m giving advice here that I didn’t personally use myself when I was doing a lot of dating. However, as I’ve given advice on this site over the years and talked with many people about how dates go “wrong”, I now recommend addressing the issue head on.

Steps to Address an Offended Date

I wrote an article several years ago on addressing a bad date after the date was over and much of the advice here will take the same approach. I’m just recommending the steps be taken at the scene of the crime now instead of safely behind your computer screen a few hours later.

1. Determine if you really did offend your date
Often, we’ll say things and as soon as the words leave our mouth we wish we had them back. In some cases, everything is fine and we’re relieved to realize our “horrible” comment wasn’t as “horrible” as we thought. Other times, it becomes clear that we’ve offended the person we’re talking to and the dynamic of our time together changes dramatically.

Being too quick to apologize for everything you say can be a turn-off on first dates. Because of that, if you think you said something offensive, start to watch the conversation. If a minute goes by and everything seems great (conversation still flowing well), I’d just move on and not worry too much about it. However, if your date grows cold or if you’re not sure if things are still going well, I’d continue on with these steps.

2. Identify the Mistake and Apologize
Once you realize you really have offended your date, I’d get right to it and make an apology. And don’t make defending your comment a part of the apology. I think it’s fine to explain what you were trying to say but if you defend your comment you’re not really saying “sorry”, you’re saying “sorry that you feel that way”.

Now if you feel the offense is based on a valid opinion you have but are willing to put your opinion aside (at least for the first date), simply apologize for bringing it up and let your date know you didn’t mean to offend them.

3. Try to Add Some Humor or Additional Honesty
As you apologize, it can be helpful to make fun of yourself in a small way to add some humor to the situation. Or if not adding humor, just explaining your nervousness or excitement to be on the date can go a long way. This helps your date see that you’re more than one bad comment; that just like them you’re a person that makes mistakes but is quick to address them.

4. Redirect the Conversation
Once you’ve made your apology, hopefully your date will say something like “no big deal”, even though it was to them. At that point, I wouldn’t sit there waiting for the other person to start the conversation going again.

Instead, try to get the conversation back on track yourself. If the conversation was going great earlier, try to get back to that. Or if you’re meeting a person you met through online dating, use something you know about them based their profile.

This also highlights the value in preparing for the first date conversations as when you do, you’ll be better able to respond in this situation.

Putting It All Together

So what does the above look like? Here are a few ideas:

This might seem odd but I want to apologize for what I just said about [insert sensitive topic here]. I have no idea why I would bring that up on a first date and I did a bad job of describing what I was thinking. I think I’m just excited by how well we’re getting along and did a little too much talking and not enough thinking. So sorry about that. But at any rate, earlier you were talking about your experience as a dance major and that was really interesting. Isn’t the training around that intense with school work added?

So in the example above, it’s more about being honest than humorous and trying to recover from discussing a sensitive topic that you might not agree on but isn’t really worth worrying about just as you’re meeting each other. Here’s another idea:

Hey let’s play a game: let’s count the number of stupid things I can say in 30 minutes. Or maybe I could just apologize and we can start that conversation over? That didn’t come out how I meant it to and I’m sorry. I’m always a bit nervous on first dates but I promise I gain better control over my mouth as time goes by! What were you saying in regards to your family again?

Here I’m trying to give an example of a bit of humor. In both cases, it’s really about pointing out the mistake with the hope that the date can get back on track, however…

Recovering from a Mistake isn’t Always Possible

You’re going to meet some people where if you say something, there’s no recovery. Sometimes this is because this issue is so sensitive to them. Other times, they might just be looking for that “perfect” person to date and if you say something that offends them, they will give up any thoughts of dating further.

But that’s okay and I don’t think these people are in the majority. It’s good to recognize that with some people, recovery is impossible. However, with many other people, an apology and some honesty can help you recover. Even if it only helps the conversation get moderately more comfortable, that’s better than knowing you made a mistake and doing nothing about it.