If You Want A Second Date, Don't Ask These 5 Questions On The First

First dates are meant for getting to know someone. But if you ask these questions on one, you might not hear back from them.

Last updated on Mar 31, 2023

young couple sitting together at amusement park oneinchpunch / Shutterstock

By Dr. Seth Meyers

When you first meet someone you’re interested in, it's perfectly normal to want to know everything about this new person. There are usually some pretty loaded questions you’d like to ask — the key is to know when and how to ask them.

RELATED: How To Make A Man Miss You

Take a look at the list below and you’ll quickly see why you should avoid asking any of these questions in the first month of dating.


After the two of you have been together a while and know each other better, you’ve earned the right to ask such private inquiries. You need to know that asking any of these questions too early usually backfires anyhow because most people will lie or embellish the truth because they don’t truly trust you yet.

Here are 5 questions to not ask on a first date, if you want a second:

1. How many people have you been intimate with? 

It’s fair to suggest that you shouldn’t ask this question in the first month. But, it’s also worth considering whether you should ever ask this question!


I don’t think it’s a good idea to ever ask anyone this because the response might unleash obsessive or insecure thoughts on your part. At the same time, it’s certainly your right to ask— just remember that it’s not your right to demand an answer.

If you ask this question, don’t do it the first month. Wait until you know each other better and then frame the question in a general way — ask, “Have you had a lot or a little sexual experience?”

RELATED: 12 Things Women Wear That Men Can't Help But Love

2. Have you ever tried any drugs? 

We all understand that drugs can be very bad for you. And yet people continue to experiment with substances every day. If you ask this question in the first month and your date has experimented with one or more drugs, odds are that your date won’t tell you the whole truth.


The best way to figure out if your date currently dabbles with or abuses drugs are to watch his or her behavior closely in the first month. For example — when you’re at dinner — does your date have an alcoholic drink or two or maybe five? If your date drinks alcohol in a binging manner, there's a decent chance that he has a substance abuse problem or that he's tried a drug or two.

3. Did your ex break up with you or did you break up with your ex? 

First, you probably agree that this question reflects an overly simplistic approach to relationship dynamics. In junior high, there’s usually one person who gets “dumped.” But adult relationships are more complex to the point that a relationship that ends usually ends for a few different reasons. What’s more — adult relationships don’t usually end because just one person is unhappy.

If you want to know more about why your date’s last relationship didn’t work, wait until you know each other better to ask for an honest appraisal of why things ended.

RELATED: 10 Dating Mistakes Even The Smartest, Savviest Women Make


4. Have you ever cheated on someone?

This question is especially tricky. First, everyone understandably believes that cheating is wrong — but you really should know the reasons why a person cheated before deciding that they’re altogether bad news. Yes — people make mistakes — but some men and women learn to correct their behavior as a result of making major romantic mistakes.

Asking your new date if they ever cheated is fair game, but you must understand that you'll not necessarily get a truthful answer until you really, really know this new person. Who would admit to such a transgression so soon? Even people who cheated and learned their lesson will fear telling you the truth for obvious reasons — so don’t force them into a position of lying.

5. Are you attracted to (insert name of a friend, coworker, or anyone else)?

As a relationship therapist, I firmly believe that it’s important to understand that being in a monogamous relationship doesn't mean that you cease being attracted to every other human being.

Once you have a trusting and established relationship with someone, it can be healthy to confess an innocent crush on someone you would never end up being with. But don’t ask this question in the first month of dating — there simply isn’t enough trust yet to share such private thoughts and feelings.


The ultimate rule for the first month of dating is to keep cool, calm, and collected — see the new relationship in perspective, no matter how much you like that person or how much your sixth sense tells you "This Is The One." Be patient and tone down your hope for the future. And trust that the relationship will become exactly what it's supposed to be.

I wish you well!

RELATED: The Perfect Age To Get Married, According To Science


Dr. Seth Meyers is a licensed clinical psychologist, author, and TV guest expert. He treats a wide range of issues and disorders and specializes in relationships, parenting, and addiction. He is the author of Dr. Seth's Love Prescription: Overcome Relationship Repetition Syndrome and Find the Love You Deserve.