7 awkward questions you should ask on a first date -- and 3 you really shouldn't

There’s plenty of debate about what you can and cannot ask on a first date. Some people say you shouldn’t go in too hard with the interrogation because it will make your date think you’re desperate. Others say the probing questions help you really learn about each other.

Ultimately, it’s hard to know what to do.

According to Erika Ettin, a dating coach and the founder of the dating site A Little Nudge, it’s best to keep things light the first time you meet someone.

“A lot of people love to compare their sob stories, like woe is me, tell me about your divorce, when was your last relationship,” she told Business Insider. “Let’s see if you like each other first … You want to learn who the other person is today. You can get to know them, then learn more about the past.”

On the other hand, if you date a lot, you might not want to rehash the same questions. You might have run out of patience and want to know some quick-fire ways to see if someone has potential, without sending them running.

Scroll down for seven “awkward” first-date questions you can ask to set up a more interesting conversation – provided you ask them right – as well as three you should never ask, just so you’re absolutely sure where to drawn the line.

1. DO ask: ‘What are you looking for in a relationship?’


On a first date, this seems pretty obvious., but a surprising number of people are too timid to ask. According to the dating site eHarmony, it’s important that you determine whether your date is looking for someone to settle down with or a quick fling before you invest emotionally. At the same time, you should think about what you’re looking for too; otherwise you’re just wasting each other’s time.

2. DO ask: ‘Am I what you expected from my profile?’


If you met on a dating app – which, to be honest, basically everyone does now – you will probably have analysed each other’s profiles excessively. Some people are transparent and you get exactly what you expected, but others come across completely differently on their profile than in person.

Sometimes it doesn’t matter and you feel a spark anyway. Other times you can feel a little cheated, because you don’t really know how to talk to the stranger you’re sitting with.

But even if this happens, it doesn’t have to be a waste of time.According to Elite Daily, it’s a good way to get feedback. For example, you can be honest about the fact you didn’t feel the chemistry, and you were misled by someone’s profile. Even though you’re saying no to a second date, you haven’t wasted their time.

3. DO ask: ‘What’s something I should know about you?’

This question can be quite a smart move, because it allows the other person to be as revealing or as reserved as they like.According to eHarmony, it gives you a glimpse of who they really are.

During a first date, people may be more willing to be open about who they are, what they like, and if they have any unusual habits. You haven’t invested in each other yet, and you have relatively little to lose.

“Use this to your advantage,” eHarmony suggests. “Ask them to reveal something that they may not reveal otherwise … It’s better that you know these answers early on before you get too invested.”

4. DO ask: ‘What do you think of [insert deal-breaker here]?’


Some people say it’s a bad idea to get into anything too serious on a first date. On the other hand, if you have some really firm beliefs on certain topics, which you consider deal-breakers, you might want to get them out the way.

For example, if you’re super left-wing, you might want to ensure you’re not dating a Trump fan. Or if you love meat, you might want to figure out if someone is completely vegan before you take things further. Of course, people with opposing views can certainly get together, but for some it’s just not an option. After all, everyone’s different.

5. DO ask: ‘Are you happy with that?’


If you’re looking to take the conversation a little deeper, when someone has told you what they do, or where they are in their life, you can simply ask: “Are you happy with that?”

It’s a perfectly innocent follow-up, and you’re not suggesting anything by it. But their answer can tell you a lot about who they are. Either they will appreciate the opportunity to talk about themselves a bit more, or they won’t. They might be defensive, but that’s a bit of a red flag in itself.

“As long as you’re not asking the question judgmentally, there’s no reason why they should be offended by it,” says one article on Elite Daily. “You have a right to know whether you’re about to get involved with someone who’s more passive than you’d like.”

DO ask: ‘Do you want to meet up again?’


If the date went well, you’ll probably want to see each other again; that’s how dating works. But when it actually comes to it, it can be tricky to work out how and when to ask the person out again. It leaves you vulnerable, because you’re basically saying “I like you!”

Overall, it’s better to arrange to do something while you’re on the first date, rather than wait around to organise it by text. Otherwise you leave yourself open to ghosting.

According to eHarmony: “If you don’t ask, you won’t know, and if you are the sort of person who can’t bear to be left wondering whether they will call or not, it might be better to come right out and say it.”

6. DO (maybe) ask: ‘So when did you last get tested?’

We’re not suggesting you blurt this out as soon as you sit down. That would be weird. And a little intense. But sometimes, a first date can go really well. And as Elite Daily points out, many people wait until they are in the heat of the moment before they bring up STIs – if they bring it up at all.

“It gives them a heads-up that this is important to you, and some more time to get tested before your next date if they haven’t been in a while,” the article says. “For another, if they react with shock or judgment, it’s a red flag that they might not take safety as seriously as you do.”

1. DO NOT ask: ‘Why the hell are you single?’

This question may seem flattering, but it’s really not. It actually just suggests there’s something wrong with being single. Or, even worse, something wrong with you.

“Being single is not a crime,” Ettin said. “In fact, it’s a valid life choice that many people desire … as if one thinks you’ve been single since the day you came out of the womb. The reality is that we never know the other person’s story.”

It also suggests that being in a relationship is everyone’s ultimate goal, which isn’t necessarily the case. Just because someone is unattached, doesn’t mean they are desperate for a relationship, or they are lagging behind everyone else.

2. DO NOT ask: ‘Do you want kids/want to get married/stay in the area, etc.?’


According to Ettin, this stuff is just far too intense for the first time you meet someone. There’s no rush, because if everything is going well then you’ll have plenty of time to work out the rest.

Also, it might make you come across as a bit desperate. That doesn’t mean that you are, but you want to present your best self when you’re meeting your partner for the first time, and fretting about the future probably won’t do that.

“Let’s see if you have rapport before you decide to have kids together,” Ettin said. “Don’t put the cart before the horse. One step at a time.”

3. DO NOT ask: ‘How much money do you make?’

Mladen Mitrinovic/Shutterstock

This one is just rude, and hopefully you understand why. It’s No. 1 on eHarmony’s list of 20 questions you shouldn’t ask on a first date, because it just makes you come across as shallow. Hopefully nobody actually asks this, but it’s better to be safe than sorry.

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