How To Get A First Date Right As A Single Parent

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Dating for the first time as a single parent and feeling lost and confused? Award-winning Dating & Relationships Expert Hunt Ethridge gives us his top dos and don’ts for first dates as a single parent.

couple holding hands over coffee on a first date
Photo by Priscilla Du Preez 🇨🇦 on Unsplash

First dates can be nerve-wracking. Two relative strangers, sitting down to suss each other out, trying to imagine a future with each other. Most of us don’t know a better way.  But I assure you, there is definitely a better way to date! Like most things, dating is a skill set that can be learned, practiced, and improved. But many well-meaning folks will give you the advice, “Don’t worry, it’ll just happen….” Nothing “just happens” and we can all help ourselves to maximize our benefits! Let’s start with some tips and go from there…

6 Dos and Don’ts of a First Date

Do keep it short

At the beginning, it is much better to leave someone wanting more than to overstay your welcome.  I have personally watched two people chatting up a storm in a bookstore, having a nice little interaction and flirting, etc.  But the guy was so excited that it was going well and so, naturally, wanted to stay there. But after 5 minutes or so, I could see the woman trying to figure out how to get out of the conversation.  It had gone on too long.  If he had “gotten in and gotten out” a bit, there could have been more of a future.

Same thing with first dates.  It can feel awesome and exciting and wonderful, so the logical thought is to keep it going until it’s not fun anymore. But at that point, well, it’s not fun anymore. Give yourself an hour for a good first date. Schedule something after it, so it will give you a real reason to end the date. Don’t spring it on your date, feel free to say something like, “I’d love to meet, I have a workout class at 3, so let’s meet beforehand.” You always want to leave them wanting a little more and excited to see you again. 

Don’t look up everything about them

I know that we are all guilty of stalking people a bit on social media. Whether it’s an ex or former friend or an old schoolmate, sometimes it’s fun to check up on them. The same can go for dating. As you start to get to know someone, it’s normal to want to learn about them. So you whip out your phone and start poking around the web to see what kind of digital footprint they have. Within a few hours, you might know “everything” about them.

But you’ll have no context for anything and you’ll take away the discovery part of learning about each other. Let them be the one to tell you about their trip to Nepal, let them be excited to tell you about their brother’s cool job, and let their past die! You are not a Private Investigator and frankly, people don’t really react well to you knowing all about them. Yes, I can go on Zillow and find out how much all of my friends paid for their houses. But I imagine if I just brought that up in conversation, it wouldn’t really be appreciated.

Do an afternoon date

There’s a lot of back-and-forth over the coffee date. It’s been called the “pre-date date,” some cultures think it’s totally cheap and for others it’s a necessity. I think it is great because, like my previous “do,” it can be a short date where you find out if there’s any actual chemistry in real life. It doesn’t have to be coffee, it could be a walk in the park or an exhibit opening, but the main thing is to have it during the afternoon. It is a much more lighthearted time of day, more things are available and it’s safer for everyone.

Plus it removes the “will we or won’t we” mental juggling act of wondering what will happen when the night ends. Is he going to ask me to come up? Does she expect me to ask her home? Is it too early? Too forward? Once you know you have real chemistry and you had a great little afternoon date, then you can schedule the next one in the evening and have to go a little longer.

Don’t overshare, keep it light

As I teach my clients, dating is a mix of biology, sociology, psychology and anthropology. One of the sociological things we tend to do is consider the first date an interview. The point of a first date is to have FUN and get a second date. That’s it. It is not an interrogation to find your next life mate! When you are learning about someone, it’s natural to want to know the answers to some big questions. But the first date is not the time to ask about their divorce or jump into politics. It’s the time to fan the flames and see if there is a spark, not to completely blow it out!

At the same time, the other person may not have gotten that memo, as you dear reader, have a higher Dating IQ! We can’t always predict exactly what inane or inappropriate question we’ll get, but we can prepare how we are going to respond when we get one. “Good question!  That’s something I’m happy to tell you down the line, but today I just want to have some fun. So if a zebra wasn’t striped, do you think it’d be better polka-dotted or plaid?”

Do be unexpected

I’m not saying to go wild and crazy (unless that’s your style!). But in romance and relationships predictable = boring = death of romance. Most relationships end with a whimper and not a bang.  Things become too predictable, too routine, no new memories or things to look forward to. We as humans love variety and it keeps our brains younger and sharper. Doing new and unexpected things feeds that desire.

It doesn’t have to be big things. Rock a bold look. Have a funny joke. Be a little irreverent. Take her through a walk that has some fun things to point out. Tease him a bit. Do an impulse buy on the date.  Not only will it be something interesting for the date, but it shows her the type of person you are.  They will look forward to the next time, wondering what new thing you’ll do!

Don’t ask boring questions

So many times, when you sit down to meet someone new, you cycle through the same boring set of 5 – 10 questions.  “What do you do?  What are your hobbies?  Where are you from?  Do you have family?  Where’d you go to school?  Etc…” We’ve heard these questions so many times that we’ve lost any joy in answering them. Also, they are all logical questions. And a relationship is emotional!

Instead, ask positive emotional questions. Instead of “Where did you go to school,” ask “What was the funniest prank you saw in college?” Change, “What do you do,” to “When was the last time your boss praised you?” When you do this, you give people access to their own happy memories. If they are thinking of these happy times, their emotions will also become happy as emotions and memories are linked. And everybody wants to be around people that make them feel good!

The most important thing is just to get out there and get some dating experience under your belt!  Find out what people like to talk about.  What stories do people respond well to?  Like any skill set, the more you practice, the better you get at it.

Join Hunt’s Frolo Meetup ‘Navigating dating & creating chemistry’ on Thursday 9 May at 8pm GMT.

Hunt Ethridge
Hunt Ethridge

Hunt Ethridge is an award-winning international dating and relationship expert with over 15 years experience helping people become the best, most dateable versions of themselves.  While the focus of his coaching is on making someone empirically more dateable, the lessons learned translate very easily into personal and professional lives. The emphasis is on confidence building, leadership, image & style, conversation skills, creating chemistry, reconnecting with fun and more. Contact him for services at, or follow him on IG @QuestForAdvice.

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