5 Funny First Date Questions for a Successful First Date

A man asking funny first date questions.
Charm your date by asking funny first date questions.

Congratulations! You’ve secured a date with a special someone. Now comes the hard part: impressing them.

Taking someone on a first date can be nerve-wracking. After all, it will determine the possibility of a second date, a third, and even a relationship. And if you’re the timid type, then you’re probably worried about making a good impression. You can have a list of what to do and where to go but sometimes plans pan out differently. However, you can never go wrong with funny first date questions.

So what makes asking funny questions for a first date the best way for a successful get-together? Not only does this ease up first-date jitters, but it also breaks the awkward silence and sets a different vibe to the date. Cyndi Lauper once sang, Girls just want to have fun. This is especially true with Thai women, and in what way can you show them that you’re fun?

Trading funny questions with each other can be a great bonding experience that will ensure another date. This can be a means to opening up a new discussion that will provide the date something to converse about brushing off small talk and awkward silences. Funny first date questions will help you navigate smoothly through this intimate engagement with a special someone who may or may not become your life partner.

So, are you ready to score that second date? Let’s jump right in.

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What are Great First Date Questions that are Funny?

People crave connection. That’s why we date, right? To find a connection with other people. One study found that the more a woman laughs at a man’s attempt to be funny, the more likely she is interested in dating him. Even a previous study affirmed that women appreciate a man’s humor which is often cited as an important trait when finding a long-term partner. It also cited that when a pair laughs together, the more they are interested in each other. But what are funny first date questions to ask a girl?

A man asking first date questions that are funny elicits a smile from his date.
First date questions that are funny will keep your date hooked all night long.

Here are funny questions for a first date to give you a head start:

1. What’s the most embarrassing thing to happen to you on a first date?

We’ve all had our fair share of embarrassing moments during dates, especially during first dates. This funny first date question is a great conversation starter that will lead to a deeper conversation. This will break the ice and have you both giggling for hours. But in order for this to work, you need to share an embarrassing memory yourself.

What’s more, you’ll be able to identify what another guy did wrong to avoid it in the future.

2. What talent do you have that people find preposterous?

When asking your date about their talents, singing or dancing are the common answers that won’t prompt further conversation. Use this question instead. People are full of talents, talents that aren’t always deemed useful but can be fun and fascinating. By asking this question, you’re allowing your date to know you are interested in her and not just fascinated by her outward appearance.

3. What is your most embarrassing memory?

Asking your date about their most embarrassing memory is a great icebreaker, but it might not be a befitting question for everyone. This type of openness doesn’t come easily to everyone, especially for someone to share this intimate detail with someone they’ve just met. If you find your date hesitant in answering this funny first date question, put them at ease by sharing your missteps. Sharing less-than-perfect moments helps your date feel closer to you and encourages connection. Hopefully, she’ll have a giggle and open up on her own.

A woman laughing at a man’s funny question for a first date.
Asking funny questions on a first date is the key to a woman’s heart.

4. What’s the corniest pickup line a date told you?

Pickup lines have a bad reputation for making people roll their eyes, but they can be helpful to your advantage. Although corny pickup lines don’t always make hearts flutter, they leave a lasting impression. By asking this question, you’ll unlock your date’s memory that will make her laugh.

5. Have you accidentally farted in public?

This is a great funny first date question, but only for certain women. It is unbecoming and somewhat taboo to fart in public. Women who are more conservative and timid may not take this as a funny question for a first date. Someone extroverted and open might be the best person to pop this question to. Tread lightly and determine if your date will find this question funny.

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What are Bad First Date Questions that aren’t Funny?

Funny questions are amazing conversation starters, but there’s a thin line between funny and inappropriate. So what can be considered tasteful but funny questions to ask on a first date?

Before asking your date funny questions, take into account your cultural differences. What may be acceptable in your country might not be acceptable in theirs. Thai people in general, take their religion seriously. Avoid overstepping boundaries, especially when it comes to their religion. It’s best to leave religion and beliefs for serious conversations. Remember, you’re on your first date and getting to know each other. Keep questions fun and light. Simply avoid questions that are invasive and disrespectful as these may irreparably hurt the relationship.

First impressions count for women when deciding whether to pursue a romantic relationship with their date. So, you want to be sure that you strike up a conversation right away by asking appropriate questions.

Just remember—first dates are meant to be a fun way to bond with someone who’s potentially going to be the love of your life. It’s good to come prepared with funny questions, but try not to overdo it. Sometimes one funny question is enough to lead to longer conversations. These questions are simply a means to knowing your date on a deeper level.

A man charmed a woman after not asking bad first date questions that aren’t funny.
Secure your dream girl by avoiding bad first date questions that aren’t funny.

The Bottom Line

First dates aren’t always picture-perfect. It’s normal to have a bit of awkward interactions and failed plans, and that’s okay! English isn’t Thailand’s first language therefore she might not be receptive to your questions. Be patient, learn to pick up on signs, and enjoy each moment. In some cases, don’t prolong the agony of trying to prove yourself worthy of a second date if your date isn’t receptive to your funny first date questions. Honesty goes a long way. Your date might appreciate it should you decide to part ways sooner than you planned.