Before you start dating, you also need to understand what exactly you’re looking for. This will ensure the planning aspects of any date go smoothly. Besides, dates can be exhilarating or nerve-wracking. There’s the matter of what you’ll wear (check out Date Night Preparation-Men’s Edition & Date Night Preparation-Women’s Edition), what you’ll do (use a site like, and, of course, what you’ll actually talk about—read on for more on this. 

The conversation starters and tips below will help avoid your date from drying up before you’ve ordered your first drink. You don’t need an index card or a script but go on your date with a plan to help reduce nervousness. You may need to pivot and that’s completely ok, be natural. This is a time to get to know them and for them to get to know you. Remember, humor and humility are excellent methods to demonstrate vulnerability while also displaying your human side.

Most of the scenarios and topics below are centered around first dates and casual dating. Although, long-term and married couples can use the topics below as well – spin it and apply them to your date night. We’re all humans and we can become interested in new things.

Pay Attention

Before we dive into conversation topics, make sure you remember to pay attention to how they respond to you. While you’re in a conversation take note if they keep the conversation about them or if they talk about you. If they stay on themselves, this can be a red flag that either they’re self-centered or it could simply be that they’re nervous and are rambling. Rambling is normal with nerves. If you think they could be nervous, continue to take note of their responses the more dates you go on with them. If the conversations continue to be about them, you have your answer. 

It’s also crucial to pay attention to their real responses so you don’t waste your time if you’re looking for something serious. A person’s comments can reveal their true colors or hidden intentions. If you met on a dating site, ask how long they’ve been on a dating site and what their experiences were?’ What was their response? If it’s something like ‘there are so many fools out there’ or something like that, this is considered a dismissive response and a red flag. If it was something like ‘I’ve met some cool people and had good and bad experiences.’ This is more of a level-headed response. 

One more thing to note about their responses, how much do they blame everyone or everything else, like exes, employers, friends, family, etc., for anything less than ideal that happened in their life? If they are blaming everything else but themselves, they have no accountability for their actions or what they cause. If you pursue a serious relationship, they will likely start blaming you for their problems – the cycle repeats itself.

Basics, Build & Explore

Basics, Build & Explore - Find The Nite Nightlife Search Engine

If this is your first date, 120th date with your spouse, or anywhere in between, dates are meant to be exploratory. Always start with the basics to get to know this person better. Start with topics about hobbies, passions, and dreams. You can even talk about something in your immediate surroundings to get the conversation going. This can help you segue into other topics. 

If you’ve had virtual or phone conversations with the person you’re going on a date with and you know a few things about them, expand on what you learned about them. If you met on a dating site, talk about something they put on their profile. If you were set up by a friend, use this as fuel to start the conversation on how you know this mutual friend. Deepen your relationship as you gain trust.

Unpack who they are

Topics regarding their Hometown, Family, Talents, Travel, Memories, Favorite Things


A person’s hometown can reveal a lot about the type of upbringing they had or how they raised their children if they had any. Asking where they’re from is a good conversation starter. This opens the door to a discussion on shared or dissimilar cultures, as well as sharing more personal details about your upbringing. Whether you grew up in different contexts or share the same cultural history, discussing it might reveal fresh insights about each other, and you may have more in common than you realize.

Family and Friends:

If you haven’t already asked about their family and friends, it’s probably a good idea to ask. This will give you insight into the type of relationship you can expect to have with your date and their family if things get more serious. If their answer isn’t exactly pleasant, you can keep it positive by responding with something like “wow, that seems difficult. How did you overcome that?” 

Take note of the friendship lengths and closeness. While doing this, remember, making friends as an adult can be tough because we have responsibilities and some of us have people who rely on us. So if they recently moved to the area, don’t expect them to have long-term friends they hang out with regularly. And, of course, if they’ve been through a divorce, that adds to the issues. If neither of these applies to why they don’t have friends, this can be a red flag – tread lightly and ask what happened.

Skills and Talents:

We all have skills and talents. Ask them what they’re good at or if they have any hidden talents. This can reveal how much responsibility they take for their lives. It also shows if they follow their passions and create opportunities or if they just ride the wave and wait for things to happen. If you have these gifts, use them. Don’t let them go to waste.


We all know at least 1 person that has a desire to travel the world for the rest of their life. Maybe this person is you or maybe you prefer to stick to where you live. Either way, this topic can help you discover if you are compatible. If you both like traveling, this broadens your conversation into places you’ve been and places you want to visit. You may even have a destination on your bucket list. Maybe this person is the perfect travel partner to check that off. 

Most Memorable Experience:

An icebreaker that is used when meeting new people, whether it’s work or personal life, is asking what their most memorable experience is. This can help them open up and share something personal that meant a lot to them. It can lead to a variety of unexpected but fascinating talks.

Favorite Things:

Everyone has at least 1 favorite thing. It can be any type of food, music genres, artists, movie series, games, hobbies, etc. The conversation can go in so many directions and there’s an unlimited amount of topics. 

ambitions & Deal-breakers

ambitions & Deal-breakers - Find The Nite Nightlife Search Engine

“Good Life” Concept:

Every one of us has a vision of what our ideal existence might be like. Perhaps it’s purchasing a home, raising a family in the country, paying off debt, or winning the lotto. What is it for your date?

If this is your first date or you’re still going on dates but aren’t official yet, find out what their concept of a good life is and their ambitions to get there. If things are serious, you can ask them something like, “ a few years from now, what things in life would need to happen for you to say things are great? Pay attention to their answer, are you in the equation of that? This will let you know if you’re likely wasting your time.

A person’s choice usually stems from their core values. This is where you want to dive into your date’s intellectual viewpoint. Do they have a spiritual and ethical core? Does it match yours? These are things to think about when dating a person.


Everyone has some deal-breakers when it comes to the dating world. We’re not talking about little stumbling blocks like a predilection for brunettes. However, certain things are unavoidably non-negotiable, such as the desire to have children or the requirement to reside in a specific location. These are things you should ease into and not bombard your date with major life questions from the start. But these are things you need to address sooner rather than later.

you can leave

You can Leave - Find The Nite Nightlife Search Engine

Check-in with you during your date. Are you enjoying the date? Is your date amusing? Remember, your time is valuable, just like theirs. There may not be a spark and that’s ok. If there isn’t a spark, you can say. “It was wonderful meeting you. Thank you so much for taking the time to come out with me. I’ve got another commitment I have to get to.” The date doesn’t need to linger on because you feel obligated to stay. You only owe your date respect, and usually, there’s always a graceful way of ending the date.

Remember, this is a date, not a job interview. You don’t need to put on a facade and pretend to be someone you’re not. Go into this date as your true self, be natural, engaging, lighthearted, and confident in who you are. Conversation starters can be beneficial in making sure your date goes smoothly, especially if your nerves are running rampant.