First dates are a lot like job interviews in that you need to present your best self in order to move forward. Over time, your true self, all the bad and good, will come out, but the hope is that by that point, they already love you and aren’t willing to let you go over a few flaws. You’ve got to make them fall in love first, though. This isn’t to say you should change who you are at all, and definitely not that you should lie. It’s just that dating culture is inherently trying to impress someone by showcasing the best parts of you and being on your best behavior. That being said, here are 18 questions and statements that are best reserved for later in the relationship (if at all) and ways you can gauge the answers without explicitly asking for them.
How Much Money Do You Make?
Everyone has different expectations when it comes to their ideal partner’s financial situation. Some people expect someone to make roughly the same amount as they make, some expect someone to support them, and some just want a partner who enjoys what they do. The point of dating, though, is to find true love, and you’ve got to go in with an open mind. There are always indicators of someone’s financial status, but unless they are extreme, try and put concerns aside and focus on the conversation and chemistry.
I Have a Lot of Baggage
Maybe you’re going into dating after a lot of traumatic experiences or bad past relationships, and you’re anxious about that. These are all things you should absolutely talk to a long-term partner about, but not until you’ve gotten more comfortable. It’s not just so you don’t scare them off, but so that you can feel emotionally safe baring your soul in that way.
Are You on Any Medication?
Medical stuff, unless it’s extreme, should probably not be a topic of conversation on a first date. Whether you are curious about the person’s mental or physical health, you, unfortunately, will just have to wait until later on to determine what’s going on there.
What’s Your Biggest Secret?
Maybe you’re the kind of person who enjoys getting into the deep stuff early on to see if you mesh with someone. That’s great, but this is a little too far. They could be put off by your bluntness, or they could end up sharing something really intense that makes things awkward. Secrets are often meant to come out in natural ways over the course of getting to know one another.
I Have a Criminal Record
If you’re a big-time drug dealer or a convicted murderer, that might be a different story, but if you’ve been convicted of drunk driving once in your 20s and you learned from it or you stole from a Sephora during college and got caught, these aren’t necessarily things that need to be on your dating resume, per se. What truly matters is how you grew from those experiences and the person you are now.
Have You Ever Had an Abortion or Miscarriage?
This is way too personal to ever ask on a first date. If someone wants to share something like this, they will eventually, when they feel comfortable to do so. Pushing it is a surefire way to make them run away regardless of whether or not they’ve experienced this.
How Soon Do You Want to Get Married?
It’s totally understandable to have a certain timeline in your head and to want to get married sooner rather than later, but asking someone this on an early date is likely to terrify them, even if you don’t mean, “How soon do you want to marry me?” If they seem like the kind of person you’d want to marry someday, let it play out a little slower.
I’m Still Figuring Out My Sexuality
Whether this is something that weighs heavily on you or something that you’re completely cool with, it may not be great to say on date #1. There are likely exceptions to this rule, so trust your intuition, especially in queer settings where the idea of sexual fluidity is more accepted and normal to talk about.
What’s Your Credit Score?
You need to know someone’s credit score before you bind yourself to them legally in some way, like signing a lease or getting married. You simply don’t need to know that on a first date.
Are You in Debt?
Similarly to the above, this is one that you do need to know eventually, but asking so early on would come across as very rude and socially unaware. These are things you can uncover over time.
What is Your Biggest Regret?
This question could be extremely triggering for some people. On a first date, you’re supposed to be having fun and getting a sense of what the other person is like, their interests, and if you have chemistry. Going this dark would most likely plummet a date into a black hole forever.
How Many People Have You Slept With?
Honestly, adults probably don’t need to discuss this anyway. What matters is being open and honest about potential STDs when and if you two become sexually active. Other than that, someone’s sexual history does not need to dictate the current relationship. That’s why it’s called history.
Have You Ever Cheated on Someone?
This is very important for a lot of people to know, but asking on the first date might come across as intense and perhaps make you seem a little more emotionally invested in the person than you should be at this juncture. Definitely not a bad question to ask, but save it for a few weeks or months in.
Do Your Parents Get Along?
Family dynamics can be a really tricky thing to walk into, but asking about them on date #1 could both make you seem too serious too fast and potentially trigger your date. If you’re really curious, find a natural way to talk about your family, and maybe they will chime in about their own.
How Much Do You Weigh?
The quantity of someone’s weight doesn’t matter, period. Everyone is permitted to have their personal feelings about who they are attracted to, but you can gauge that based on looking at the person and either feeling attracted to them or not. A number on a scale has nothing to do with it, and asking someone this will reduce them down to their weight when they are worth so much more than that.
What Was Your Ex Like?
We’re all curious about our new partners’ exes, and it’s only natural! We are socialized to compare ourselves to others who might have once held the attention of that person. You can totally ask this question when you’re more secure in the relationship, but asking on the first date will come across as too personal and maybe even creepy.
Do You Have Any Mental Health Problems?
It’s truly just inappropriate to ask someone you barely know this question. In fact, 1 in 5 adults experienced some sort of mental illness in 2021, so you can assume it is quite likely your date has or is going through something like this. Asking will probably read as judgmental. Instead, ask about their hobbies, friendships, and other interests. You will likely get a sense of what is going on in their head.
How Long Until We Can Sleep Together?
There are other ways this can be said or inferred that should not leave your mouth when you’ve only just met someone. It puts pressure on them to have sex with you and will likely make them uncomfortable regardless. It’s best in these instances to follow the natural cues and pay attention to your date’s body language before creating an unnecessarily awkward situation.
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