How to Pick Good Questions to Ask a Woman on a Dating Site

There's no denying that online dating websites are the best way to find love nowadays. Tons of platforms are capable of matching you with another like-minded person in a very short time. One last and really important hurdle you need to go through before achieving success is making the first move.

Social rules say it's the man who must approach the woman first. If you are currently in this position, sending a message to your crush may be a point of struggle. Making the first move is hard because of many factors, but the pressure is the main one. "What if the person doesn't like what I'll say? What if I seem boring? Is this the right time?" Those are just a couple of uncertainties you may face when the time to ask the first question comes. But don't worry. There are various solutions to solve this problem, and by following the tips we're going to provide you today, you'll easily master how to message someone on a dating platform.

First Question to Ask a Girl Online Dating

Good Opening Questions for Online Dating

A good opening question will make the girl remember you. In addition to it, it needs to be simple while still open-ended. Yes or no questions can immediately end the conversation if she doesn't add anything to her simple answer, which is likely.

A few good questions that follow this model are:

"What is a random fun fact about you?"

"Would you rather do… or …?"

"What's something that's beyond you?"

"What is something you're proud of?"

"What are you currently into the most?"

"Have you ever done something super crazy?"

Think of Her Bio When Planning the First Question

Taking a look at her bio is the best way to come up with a first question. Frequently she'll list the things she enjoys doing, her favorite movies, music styles, or other similar stuff. If you also like or at least understand some of those things, come up with something related to ask her. For example, asking her about her favorite band would be a great idea if she enjoys rock music. If she's into parties, check which clubs she likes the most.

Asking a question related to her bio also transmits a positive message because it means you're interested in what she enjoys. When she reads and sees how you "studied" her, she'll start seeing you as a serious prospect, and getting her into the conversation will be much easier.

Ask About Her Main Interests

If you have read her bio but she didn't include anything you can use to kick off the chat, ask her directly about what she is interested in. Be aware that the way you ask her about this may also make her uninterested.

For example, asking an extremely broad question like a simple "What are you interested in?" forces her to brainstorm a lot before answering you. There are a thousand million things she likes, so it can be hard to handpick and tell you about some of them in such a short time.

Instead, you could ask something like:

"What do you like doing after school/work?"

"What do you usually do on weekends?"

"What's funny you've done recently?"

Filter the Good Questions to Ask on Dating Apps

Many guys make the mistake of rushing way too early when they're just starting to know the girl. Everything will come at its own pace if you execute your plan correctly.

If you are still on the dating app you met, a common mistake is asking for her number too soon. You should wait a bit before mentioning personal subjects. Make sure you know each other better, and then start with this line of questioning.

It is important to ask personal (but not overly personal) questions when you're getting to know her. Think about things that are important for your relationship to work out in the first place, like whether or not she has dogs, children, or what her objectives are. If there's any dealbreaker, it's better to know it now rather than later, which would hurt more.

Questions that follow this idea are:

"Do you like pets?"

"What do you think about children?"

"What is the kind of relationship you're looking for?"

"Have you dreamt about living in a different country?"

Ask Something Interesting and Never Say Just HI

One of the most common mistakes men make when first starting a conversation is to be way too brief. A lot of people try to start their chat by saying something like "Hi," "How are you doing," or "Hello there." It's not a surprise why they don't get responses.

Starting with such a bland introduction like these makes the girl not want anything from you. Ever imagined how many other guys have asked the same question before on the same day? Or how many people already ask her if she's doing okay? So, to be selected, you must stand out.

The Best Funny Pick Up Lines to Use on a Dating App

Starting a conversation is not all about questions. Pick-up lines are a funny and efficient way of beginning a chat on an online dating site. It's a shame that very few men use this tactic, mostly because they're either embarrassed or think it's too goofy. Don't follow this path and use such lines as women love them!

Shy guys are too afraid of using pick-up lines. This kind of interaction is a bit riskier than a simple question, as some girls might not see it by the funny side. When she likes the line, your chances of success are really good. If you still struggle in this aspect, it's time to let your fears go. Real men are not afraid of breaking the ice with a pick-up line or more audacious questions, and that's why they are more successful.

Funny pick-up lines you can use:

"If I could rearrange the alphabet, I'd put 'U' and 'I' together."

"I must be in a museum because you truly are a work of art."

"Will you give a chance to the three of us? (Me, you, and love?)"

"I'm not a photographer, but I can picture us together."

"Do you believe in love at first sight, or should I walk by again?"

Use Cheesy Pick-up Lines to Get a Girl

You could also go for something more cheesy. We recommend not exaggerating too much on the sarcasm; it could lead the girl to think you're a child.

Here are some examples:

"Are you a parking ticket? Because you've got FINE written all over you."

"I think you're a good investment because you got my interest."

"Drake would call you and me God's Plan."

Let Her Do Most of the Talk

Another important thing to have in mind is that girls like to talk about themselves. Let her talk as much as she wants after you ask your open-ended questions. Talking too much about your life and interests will easily get her bored, which is something you don't want to happen.

If she seems interested in doing the talk, you can ask even more questions to make the chat flow. You don't want to flood her with questions too. As always, make sure everything you do is well-balanced and relevant.


There are different ways to break the ice when talking to a girl for the first time. What makes it tough for most guys to make this move is their lack of courage. And in a world where the man is expected to take the first attitude, being stuck in this step might mean not getting into a romantic relationship altogether.

You can choose between questions about her interests, views on relationship types, cheesy pick-up lines, and much more. We hope the examples brought to you by this guide will help you finally conquer your crush's love!

Author: Jennifer Lorusso
Jennifer Lorusso is a recognized dating and interpersonal relationship expert. As a woman with Psychological degree, she utilizes both her whole life training and her incredible life experiences to serve her readers. She is known for her approachable manner and empathetic abilities. She trully believes that everyone can find true love as long as they believe it is available to them.
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