24 tips for meeting an online date for the first time

So, you’ve made a killer dating profile and swiped left through the seemingly never-ending stream of profiles with “‘6’1’” or “coffee addict” in their bio until you found someone who piqued your interest.

Not only was it a match, but you made it all the way through the “what’s up?” and the “I never really check this app, do you want to just text?” to the “so there’s this new spot that opened up in my neighborhood, would you want to check it out together?” and you got yourself a date!

Reality TV, *cough The Bachelor cough*, has time and time again given us a completely unrealistic example of what first dates look like.

(That said, if any of you readers went on a helicopter ride for a first date please reach out and explain to me how exactly you pulled that off).

In actual reality, first dates are much more low-key; grabbing dinner, playing mini-golf, or, in these never-ending covid times, even just having a glass of wine over Zoom.

The commonality is that, regardless of where a first date takes place, it should be exciting, fun, and nerve-wracking in all the best ways.

Read: should be.

Unfortunately, quite often first dates are awkward, uncomfortable, and nerve-wracking in all the worst ways.

For example, instead of the fun “oh-my-god-they’re-so-cute butterflies”, it’s the “oh-no-we-definitely-hooked-up-in-college-and-he-doesn’t-remember-me-butterflies”…no?

Just me? Okay, moving on.

Anyway, sprinkle the fact that it’s an online date into the mix, and the pre-date jitters only increase.

But, despite certain past experiences, I’ll say it again: dating should be fun.

Regardless of whether or not your date ends up being the one, it’s an opportunity to meet someone new, to have a new experience, to share an interesting conversation.

So read on, because while you may not be able to control the fact that your date thinks it’s unique that they got into cooking during quarantine, there are many things within your control to ensure it goes smoothly and that you head home with no regrets.

1) Find a good date spot

Pick a place or activity that is going to encourage flirtation and set the mood in the right way.

Whether you go to a local arcade for some playful competition or an intimate bar lit by candlelight, it makes it so much easier to let loose and have a good time if the vibe is right.

Coffee shops should be strictly for casual business meetings, catching up with that friend from college that you just can’t seem to shake, or pretending to work on your screenplay while you listen to moody music and gaze dramatically out the window.

So, let’s end the coffee date once and for all and do something fun!

2) Wear something that makes you feel confident

The concept of “dressing to impress” can trigger limiting beliefs or gender norms that tell you what you should be wearing to look attractive.

For example, thinking you should wear heels, or a nice button-down, or shouldn’t wear those worn in converse that you love.

The more confident you are, the more attractive you’re going to be.

So, when getting ready for the date, think about what kind of outfits make you feel your best.

If it’s a dress shirt — go for it! If it’s a leather jacket and combat boots — go for that!

Everyone is attracted to different things, and what’s most important about attraction (at least for it to be sustainable), is that they are attracted to your authentic self.

3) Practice good hygiene

So, while physical attraction may be subjective, personal hygiene is decidedly NOT.

Studies have shown that smell plays an important role in attraction.

So, make sure to take a shower, brush your teeth, and present the best (and cleanest!) version of yourself.

4) Tell a friend or family member where you’re going

While studies have proven that there are many great catches available on dating sites and apps (as of 2017 almost 40% of couples say they met online), always make sure to tell someone where you’re going and who you’re meeting.

Better to be safe than sorry!

Also, if things end up going south, you can always have them call you so you can give the Oscar-worthy performance of your dreams pretending that there’s been a “sudden emergency” that you “simply MUST attend to”.

5) Be on time

No one wants to experience that excruciating time between the moment you get to your meeting spot and the moment your date shows up where you inevitably wonder if you’re possibly getting stood up and everyone in the bar will laugh you out the door.

Show that you respect them and their time by showing up when you say you’re going to.

Save being fashionably late for the good stuff (like that party with multiple friend groups that’s awkward until everyone is kinda drunk, or like, your wedding).

6) Put the phone away

Speaking of respecting someone and their time, keep your phone off the table (one expectation being the aforementioned Oscar performance).

No one wants to have a conversation with someone who’s looking down at their phone, and it sends the message of being disinterested — which doesn’t foster an environment in which a connection could thrive.

So, don’t be an asshole and excuse yourself to use the restroom so you can text your friends on updates from the stall just as any respectful person would.

7) Leave the high expectations at the door

While certain expectations are completely normal to have (please refer above to practicing good hygiene), keep an open mind until you actually get a chance to know them a little bit.

Don’t start the date with predetermined expectations such as “they need to be tall” or “I’ll only go out with them again if I could see myself being with them for the long term”.

If you do, you’re just setting yourself up for disappointment and not allowing yourself to potentially be pleasantly surprised.

Remember, it’s okay if they don’t end up being the one!

In fact, it’s very normal if they don’t end up being the one.

But, if you walk in and decide they’re not the one within the first 10 minutes, you’re running the risk of missing out on what could be a great time.

8) Steer clear of surface-level small talk

If you want to have the opportunity to form a deep connection, you have to get to know them on a deeper level.

No, this doesn’t mean asking them about their parent’s divorce on the first date is a good idea (speaking from experience here).

But, keep the discussions about how crazy it is that it got this warm in March (okay, it IS crazy though!) for your coworkers and that person in the elevator who very clearly doesn’t want to talk to you.

9) Ask interesting questions

While we want to avoid small talk regarding things like the weather, or whatever might be playing on the bar’s TV, there is a way to deviate from the normal to ask non-invasive questions that will spark interesting conversations.

Instead of asking “how was your day?”, ask them what the most interesting part of their day was.

Instead of asking what they do for work, ask them why they got into their professional career or what they love most about their job.

By asking more dynamic and engaging questions, you’ll get to see their personality shine through much faster.

10) Don’t bring up your ex, or ask about theirs

As curious as you may be about who they last dated (and why they broke up, and if they were hotter than you, and if they still look at their social media accounts), the “ghosts of relationship past” conversation should absolutely not take place on the first date.

This is the time to focus on the two of you, no exes should be haunting it.

11) Be a good listener

Don’t be the person who asks a question and then immediately zones out and starts looking around the room.

Or, arguably worse, don’t be that person who asks a question and then immediately jumps in with their own story or opinion about it.

Being an active listener will encourage them to open up to you and provide more opportunities for connection.

12) Be authentic

The biggest mistake people make on first dates is trying to be someone they’re not.

Maybe it manifests as talking about how successful their business was last year because they think that will prove their value, or as constantly slipping in literary references in hopes their date will think they’re smart.

If your business is your passion project, by all means, tell your date what excites you about it.

If you love to read, tell them about that beautiful book you just read and what it is that makes you cry every time you read it.

Just don’t say or do anything that you’re only doing or saying because you hope they’ll be impressed by it.

They probably won’t.

13) Compliment them

Despite all of the flirtation and excitement and romance dating brings, it can be a very vulnerable process.

Especially if you’re meeting someone from an online dating app or a site in person for the very first time, the idea of putting yourself out there to see if someone is attracted to you can be terrifying.

Don’t overdo it on the compliments, especially on their physical appearance, but a simple acknowledgment of what you find appealing about them, such as “you’re really funny” or “I like your shirt”, can go a long way with making your date feel reassured.

14) Be aware of the signals they’re sending

There are subtle and not so subtle ways that your date could be signaling you to let you know whether or not they’re feeling you.

If your knees brush under the table and they let them stay there, they are probably feeling a physical attraction.

If they immediately say goodbye after leaving the date spot, they are probably avoiding the chance for a kiss or a mention of a second date.

Even if they aren’t directly communicating it, there are many ways to tell if a date is going well or not.

Open body language, physical touch, compliments, and asking lots of questions are all signs of interest and attraction.

Lack of eye contact, keeping their distance, short answers, and asking for the check without discussing with you first are all signs that they are ready to get out of there as fast as they can.

Be aware of these while you’re actually in the moment, instead of playing it back in your head later when you’ll just be reflecting on your interpretation of the situation.

This can help alleviate the post-date “will they or won’t they call” anxiety and provide you with more clarity on what actually happened.

15) Flirt with them

Do you find yourself going on first dates that don’t turn into second dates because the vibe never progresses past a platonic one?

It’s probably because there is no flirting!

Far too often people are too self-conscious to try to flirt because they think they aren’t good at it or they worry it won’t be reciprocated.

If neither you nor your date ever makes the move to be flirty, then of course it’s going to stay on a platonic level.

There are so many different ways to be flirtatious and build that fun tension between the two of you.

You can flirt with body language, eye contact, or humor.

If you think you aren’t good at flirting, you just haven’t figured out what works for you yet. Check out some tips here and remember, practice makes perfect.

16) Be mindful of your body language

Just as you should be aware of your date and how they’re feeling, be conscious of what signals you might be sending off to your date.

Body language plays a big role in the ability to connect with someone.

Small adjustments like making eye contact and keeping your arms uncrossed make a huge difference in your approachability.

17) Don’t drink too much

Okay look, one tequila drink can make you a better flirt.

Studies have shown that (I did the study).

Studies (studies by me again, you’re welcome for my sacrifice) have also shown that more than three tequila drinks can make you forget you ever knew how to flirt.

No one likes a sloppy date and more importantly, if you’re meeting someone from the internet for the first time, overdoing it with the drinks has the potential to seriously jeopardize your safety.

By all means, order a drink if you’d like, but know your limits.

No matter how well the date might be going, this person is still a stranger to you in a lot of ways and it’s important to keep your wits about you.

18) Respect your boundaries

Make sure you respect your values and your boundaries during a date.

If you don’t want to have a second drink and they do, don’t let that influence you.

If you don’t want to go have a nightcap at their place, tell them you’re going home.

If you don’t feel comfortable with them being so touchy, it’s okay to say that.

The idea of setting boundaries feels really intimidating to a lot of people, when in reality it’s one of the most important aspects of a healthy relationship.

In reality, it’s just being proactive and effective about communicating your needs, and if your date doesn’t respect that it’s better for you to know now.

19) If you’re interested, show it

Along the lines of healthy communication, don’t shy away from expressing your interest if the date is going well.

While you want to be careful not to come on too strong, if you’re enjoying your time together – say so!

Being straightforward about when you’re having fun with a date, that you like talking to them, that you find them interesting can be so refreshing in this era of singles that love being elusive and playing hard to get.

20) Avoid the awkward conversations about the bill

Discussing money and bills always has the potential to be a bit awkward, so avoid that conversation and, as a general rule of thumb, just offer to split it.

If your date involves an activity, this simplifies it even further because you can just pay for your ticket and they can pay for theirs.

It’s the 21st century people!

Equality is sexy and it’s very, very hot to reject gender norms.

21) Enjoy yourself

Although the position of being your partner is a coveted role, remember, a first date isn’t a job interview.

Give yourself permission to have a good time and to be in the moment.

While it’s important to keep certain things in mind while dating, getting too caught up in the “dos and don’ts” can actually hurt your chances of a good date and just result in you being stuck in your head the whole time.

22) Don’t be afraid to initiate a second date

Do you know what else is sexy? Confidence.

If you want to see them again, let them know that.

The worst thing that could happen is that they’ll say no and you won’t see them again — which would likely be the case if you never asked about a second date anyway.

So, seize the opportunity and tell them you had a great time and would like to go out with them again.

23) Be honest and polite if you aren’t into them

Sometimes no matter how romantic the date spot was, how amazing you looked in your outfit, and how much you enjoyed the conversation, the romantic connection just isn’t there.

In those cases, it’s always better for you to be honest about how you feel. Even though it might disappoint your date, in the long term they will appreciate your directness.

It’s good to be direct, but make sure to do it gently and compassionately.

There might be a specific reason you know you won’t be compatible, but there’s no benefit to telling someone what you don’t like about them.

It’s only going to make them feel bad about themselves.

Letting them know you had a nice time tonight and liked getting to know them, but you’re not feeling the connection is all you need to say.

24) Don’t obsess about it afterward

It’s completely normal to spend some time thinking back on the date after it happens.

Unfortunately, that thinking can become a slippery slope to overanalyzing, which can take a sharp turn to self-criticism.

“Why did I eat so much garlic bread?” (because garlic bread is delicious).

“Why did I get so excited when Driver’s License came on?” (because it’s a great song).

“Did I actually tell them the story about SantaCon 2017?” (SantaCon is a tough time for everyone and it’s an objectively funny story).

This kind of thinking isn’t going to do you any favors.

It also is going to result in you spending so much time picking apart every little aspect of the date that it’s going to make you start questioning what actually happened.

Trust how things felt in the moment, the signals you picked up on, and what your initial thoughts were after you said goodnight.

If you never end up hearing from them again, it just wasn’t meant to be and that’s okay.

With the number of people who are now using online dating as their primary way to meet people continuing to rise, there are going to be so many opportunities for more wonderful first dates.

Whether your first date turns into a second date, tenth date, a new friendship, or a funny story, each one is getting you closer to finding the right person for you.

Maggie O'brien-pappalardo

Maggie is a writer, Relationship Coach, and sarcastic romantic who draws on her personal and professional experience to help others navigate the world of dating. Based in NYC, when she’s not writing and coaching she can be found traveling and romanticizing her life from various beaches and/or cities (Hawaii is next - follow along on Instagram at @maggieobp).

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