6 Tips to Avoid a Boring First Date

If there’s one thing that will ruin a date fast, it’s having a boring one. You want your first date with someone to be exciting, fun and memorable! You never want to go on a date with someone and forget everything you did and said the whole time. That will not warrant a second date. And isn’t the goal of a first date to get a second one? Don’t you want the other person to have a good time and to find you interesting?

The trouble with this is that most of us get really nervous, and this makes us shy (or worse, chatty and only able to talk about ourselves) and in turn… boring.

#1 Slow your roll with the texting beforehand
Even if you and this guy have been texting non stop since the moment you met or matched on tinder, maybe try cooling it with the texting the day of your actual date.


This way, you’re saving some topics of conversation for the first date. The date can get a little awkward if you’ve already talked about everything there is to talk about throughout the day via texting.

So save some funny stories and interesting thoughts for the actual date.

#2 No one likes small talk
Small talk is always boring, and honestly, I think it’s pretty unnecessary.

If you don’t want to talk about the weather or the neighborhood you live in, then don’t!

Choose something you’re actually passionate about and start to steer the conversation in that direction. There’s nothing more attractive than listening to someone talk about something they’re actually excited about.

#3 Find out what they like prior to the date

If you’re going on a first date with someone, you at least got their number or some contact so you can talk. This way, you get to know them somewhat prior to the date.

Why is that important? Because that way you learn some of their likes and dislikes. Then suggest things to do that will be more enjoyable for them. That way they won’t feel awkward or have to pretend to enjoy something!

#4 Ask questions… but not too many

Another way to not be boring is to just ask them questions. However, you don’t want it to seem like they’re in an interview instead of a date. By this, I mean ask questions about them but not one after another.

If they mention how much they love cycling, ask them more about that topic and what they specifically like about it. And be genuinely curious about it because that will be entertaining.

If there is a pause in the conversation, don’t immediately fill it with a question. Wait it out a little, see what your date does. Don’t immediately fill the silence with a question. But if you are ready to ask a question, here a few fun ones:

What’s your death row meal?
Or, if you’re afraid of bringing up death on your date: If you could only eat one thing for the rest of your life, what would it be? Chatting about your food likes and dislikes is really fun, plus it’s valuable knowledge to keep hold of in case you progress to cooking dinner together in the future!

If you won the lottery, what would you do with the money?
This is a fun conversation starter and helps you find out if your date is a big spender or has an entrepreneurial spirit.

#5 Do something interactive

Don’t just go sit at a movie and then go to dinner. If you really want to be fun and not boring, go on a date that’s interactive. Meaning, go on a date that you actually do stuff. Maybe a wine and painting night, laser tag, ice skating… really anything you participate in. Bonus points if it’s something where you can challenge each other!

Some fun and easy ideas are:

If it’s a nice day out, why don’t you two rent some bikes and go around the city? There’ll be lots to see, and you can adventure around the town finding out new places, together. You’ll be surprised what you can see while on a bike. Also, it’s a good way to see if your date is active and likes spontaneity.

I personally don’t love bowling, so I don’t think it’s one of the fun things to do on a date. But, surprisingly, lots of people actually like bowling. I think it’s because you have the opportunity to touch your date without coming off like a pushy sleaze bag. Whatever. If you like bowling, then I highly recommend you try it out with your date. (Preferably at a place that serves alcohol.)

#6 Challenge them

A date that’s challenging – one that makes you think – is the most entertaining of all dates. If their mind works the whole time, there isn’t any room for them to be bored. That means you should ask them things to make them think and engage in challenging topics. Or plan to do something competitive (e.g., laser tag, bowling, etc.)!

At the end of the day, remember everyone is boring some of the time. Some of the most interesting or funniest people I know are not telling riveting stories or eliciting thunderous laughter in every single second of every conversation. Part of the joy of solid relationships, romantic or otherwise, is you do not have to constantly be “on” when you are together. You get to glimpse a person’s mundane and profound thoughts and bond with them through smiles… and the yawns.

Or, you could do what I’ve been doing the last month and stay home watching Netflix thinking about every guy you’ve ever dumped and wondered if you hadn’t been such a bitch in the past if you’d be married by now… I vote you go out and try and have a fun date.

…Maybe I should call up one of my exes? 😉


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