Modern Dating Tips for the Digital Age

November 17, 2021

Are you ready to be completely honest about your dating life? You should be if you’ve found this article!

Love doesn’t always look like what we’re sold in romance novels. It’s complicated! 

We’re not here to judge — we’re fellow daters ourselves and have had to learn the hard way on how to date in the digital age. 

So here are our best dating tips and even some dating rules for every stage of the dating process!

First… We have to start with the definition of dating!


The definition of dating


You might be asking yourself (like many daters today!)... What does dating mean? It can be complex and confusing.

“Dating” can mean different things to different people, especially as the traditional definition of “dating” is constantly developing and expanding . Conventional “dating” constitutes two people in an intimate relationship. Although “dating” implies a sexual aspect to the relationship, it does not have to be. Dating can be serious, causal, monogamous, open, polygomous, short-term or long-term. 

The word “dating” is now an umbrella term that consists of many more relationship types. 

Some of the most commonly used words to describe dating are:

  • Going out
  • Together
  • Being with someone
  • Seeing each other
  • Just friends
  • Friends with benefits
  • Hooking up
  • Partners 

Now let’s get into dating advice and tips!


Modern dating advice and tips


First Date Prep!


Be honest about what you’re looking for 


Before you hype yourself up in the mirror and head out the door on your first date, take a second to ask yourself what you want out of your dating experience(s). 

Are you looking for something serious or just a good night out? 

Once you know that, make your intentions clear with the person you’re seeing. If you get that out of the way, it avoids a lot of guesswork on both ends. You’ll be able to actually enjoy their company without having to read in between the lines to know if they’re on the same page as you. 

If you find that your interests aren’t aligning – accept and express that to the other person! 


Ask questions and practice active listening 


Before you even meet someone for the first date, you’re likely texting or messaging them on an online dating app or site. Or, maybe you met through friends or in real life — either way, you’re probably communicating prior to the first date!

I know it’s second nature to memorize fun facts about yourself that you can pull out whenever the conversation lags — but try to hold back! Making the conversation more about the other person by asking questions and responding creates an environment that encourages real conversation.

If you need some conversation starters, we’ve put together a guide to top online dating questions!

You can definitely go through the usual “What do you do?” and “What Netflix show are you binging right now?” – those are classics. But think outside of the box as well.

See where the conversation takes you. Look for commonalities in your dialogue. 

And don’t be afraid of small silences – it’s okay to sit in discomfort. 

If you really having trouble coming up with small talk, it helps to rephrase or confirm what they’ve said: 

Online date: “Yeah, I am interning for this nonprofit in the city. It’s a lot of work, but I enjoy it.”

You: “It’s a lot of work?”

Online date: “Definitely, I have a lot of hands-on responsibilities like dealing directly with our clients. Do you ever feel like that at your job?”  


Have reasonable expectations 

A lot of people want to go in with low or no expectations when dating, but that can easily backfire!

As a queer woman of color, I have a lot of dating expectations for the partner I choose to be with — and that’s good, healthy even!

Personally, I look for someone who is outwardly politically aware, sensitive, and ambitious. It is important that I am with someone who, at the very least, respects my core values. I urge you to draft a mental list of what you’re looking for in a partner as well. Your list might look very different from someone else’s but having one can help you figure out if this is the person you want to be spending your time with. 


Don’t worry about who is paying

A good general rule of thumb is that whoever did the “asking out,” should be the person who pays for the date. 

But if you’re somewhere fancier or know there are power dynamics in the relationship (i.e. someone makes significantly more than the other person), think about splitting the bill or even offering to pay. 

For first dates, it’s a pretty safe bet to do something that doesn’t require extraneous finances. Try a museum, a picnic at the park, or take a nighttime ferry ride. You’ve got options. 


Share your location with someone

We’re all about safety when it comes to dating — and this is a must-do!

Whether you’re meeting someone from a dating app or have been introduced through a mutual friend, let someone know where you’re going and what you’re doing. It could be your bestie, the sibling whose sweater you borrowed, even a parent will do. Not only are you being safe, now you have someone to debrief with after your date is over. It’s a win-win. 



Sex can be cool

Sometimes you’ll hit it off with your date and want to take it further. Don’t let an arbitrary rule dictate whether you’re going home with someone. 

But, make sure you’re practicing safe, consensual sex


What should you NOT do while dating?

Ghosting won’t help you find someone

Bad dates happen and while you’re not obligated to follow up with your date, ghosting isn’t the way to go. I know you may be tempted to let the texts go unread or leave the DMs on seen but remember that your date is also human! 

You definitely don’t need to give them a Spark Notes summary of what you think went wrong, but polite closure would keep them from making assumptions. Dating in the 21st century makes it easy to hide behind a screen — resist the urge.

But, if you feel like you’re in an unsafe situation and that ghosting them is the best thing for your mental, physical, and/or digital health, then it’s okay to ghost.

Put the phone away


Again, I know the cool metal screen basically burns a hole in your pocket when you’re on a first date. The comforting feel of scrolling through Twitter or opening Snapchat just to take a glance at yourself will probably persist throughout the date but stay strong. Keeping yourself focused on the person in front of you could determine the outcome of the entire outing. I suggest putting your phone away entirely or having it on Do Not Disturb for the length of your date. Minimizing any distractions will help you stay present and even calm your nerves. 


Avoid ex-talk — Please!


This tip is pretty self-explanatory. Talking about your exes and past dating experience never makes a good impression on a first date. It creates weird tension in the room and is usually followed by prolonged and awkward silence. To avoid discussing your exes — literally find anything else to talk about. What book are you trying (and failing) to read? Which TikTok is stuck on an endless loop in your brain? Starbucks or Dunkin? ANYTHING!


Think about a drink, just don’t pregame


First dates can be intimidating and there’s nothing wrong with trying to ease your worries with a drink. However, I do suggest that you and your date account for any tipsy encounters. A drink or two together can help calm the nerves, but save the pregame for another night. Drinking without your date can come across as sloppy. You may lose some of your foresight if you show up to the date already drunk. Not a classy move and can really turn someone off. 



Don’t get carried away


There are moments after your first date when you think you’ve found the one! Maybe this person was everything you’ve dreamt about and more. Next thing you know, you’re getting way too invested in a budding relationship. I know it’s exciting to get caught up in first date jitters and post-first date bliss, but remember that there’s more to this person than what you just experienced. Everyone tries to put their best foot forward on a first date, so there’s much you have yet to discover. Keep cool and keep having fun. 



Dating tips for new relationships


Keep your routine


New relationships are fun because you get to explore life with this whole other person — but don’t forget about the one you’ve already built for yourself. Too many times a person gets into a new relationship and neglects other aspects of their life: their family, friends, school, or career get sidelined. 

While it’s normal to get swept up in a new relationship or partner, remember that you have a support system that still depends on you as well. Make sure you aren’t abandoning your hobbies or interests to spend hours and hours with your new partner.   


Don’t stress about social media


Again, dating in the digital age reveals an entirely new set of hurdles to work through. When you get into a new relationship, you might be nervous to post them on your social media. Or you’re asking yourself if they will ever post you on their social media. Debating about whether your new partner is social media savvy can help you determine when/if to post them on your social media platforms. Always check in with your partner to gauge their privacy concerns as well. 


Keep asking questions 


Just because you and your partner have decided to start a relationship doesn’t mean you truly know each other. First dates are good introductions to a person’s interests and background, but there’s always more to learn. Make the effort to get to know your partner by asking questions and continuing conversation when you can. It’s helpful (and fun) to keep “dating” your partner even if you’ve already established an exclusive relationship with them. They might surprise you! 


Talk about your boundaries 


Any healthy and long lasting relationship has good boundaries and open communication. I know the conversation can be awkward or uncomfortable, especially if you are getting really personal, but it’s worth it. If there’s something you need your partner to know, it’s better to get everything out in the open while the relationship is fresh. Hopefully your partner is accepting and it is a chance to connect with them emotionally. 


Enjoy the present 


New relationships are great because it’s a blank slate. You can start over. No drama. It’s a chance to grow as an individual as well as a partner. Enjoy it! Take each day as it comes and try to live in the moment. Expressing gratitude for the time you have with your partner paves the way for a fruitful relationship. Don’t worry about 1, 3, or 5 years from now. You have this time and you should try to make the most of it.


Antiquated dating rules

Dating in the digital age is dramatically different from the dating game our parents experienced. They might try to pass down their old school rules or tips — and some might still be good while others are outdated and antiquated. 

When you’re dating, you need to define your own dating rules while communicating them with your partner(s) to be.

What is the 5 date rule? What is the 10 date rule?

Both the 5 date rule and the 10 date rule are pretty old school practices. The 5 date rule says that a woman should go on at least 5 dates with their partner before having sex with them. The 10 date rule proposes that men don't see the women they're dating as potential girlfriends or wives until they've spent quality time with them 10 times. Clearly, both of these rules are extremely gendered and place unrealistic expectations on both parties. 

What is the 222 rule?

The 222 rule is cited as a way to keep marriages or longer relationships “exciting.” It motivates partners to go on a date every two weeks, have a weekend getaway every two months, and take a week off every two years. Although this exact regime may not work for every couple, this rule helps to prioritize your relationship. It keeps both partners invested in the relationship. Essentially, it allows both people to keep dating each other — even if you have been together for a long time. 

While it may work for some, it can also be a traditional way of thinking about relationships. Partner(s) may feel like they ONLY have to do this and forget about the small, intimate moments found within the everyday relationship.


Dating questions everyone secretly has


How often should you see someone you're dating?

Like we mentioned earlier, you shouldn’t fall head over heels in love with someone after the first date. While it’s fun and exciting to get to know someone, taking it slow can actually help build romantic interest and dynamics. 

By starting slow, it also shows that you aren’t totally available to cater to them and that the other person has to deserve your attention. 

We suggest 1-2 dates a week at first and then ramping up from there. You also don’t want to see them so often you get bored or the relationship gets stale!


Is it wrong to date multiple people at once?


Every person is unique when it comes to their feelings on this question. It’s really up to you! Sometimes dating multiple people can help you figure out what you’re looking for in a relationship faster. Sometimes it is too much to handle in your busy schedule. 



When can you tell someone that you love them? 


Ohhhhh — the big question everyone secretly asks themselves. You might feel feelings of “love” super early in a relationship — sometimes it is love and other times it’s just being super twitterpated with someone new. 


Oftentimes, people set a rule that they’ll never be the first person to say it in their relationships. This can be a little toxic. 

When should you meet someone’s parents? 


Meeting someone’s family can be a big step in any relationship. This shows a lot of trust and commitment to the other person and the relationship. 


If someone invites you to meet their parents, make sure YOU are ready. There is no set time-frame for this, it’s more about how you feel about the relationship’s progression and how comfortable you are in taking this next step. 


What are the "5 stages of dating"?

This is another kind of old school way of thinking about dating and relationships — although it can be beneficial to some. Remember: every relationship is different!


  1. Attraction and romance - this is where the fireworks are happening and you’re both wooing each other! 
  2. Reality - There should still be sparks and some magic happening, but you’ve moved beyond trying to impress them to trying to be yourself around them.
  3. Commitment - This is when you truly commit to each other and growing the relationship. You may already be partners at this point but this is taking it to the next level!
  4. Intimacy - Intimacy isn’t about sex — it’s about cultivating and nurturing the love that already exists. This is where true love starts to form between individuals.
  5. Engagement - Here is when you decide to commit your life to loving the other person through all the ups and downs life throws at the both of you.


Every relationship is unique


There is no linear path to love. Whether you’re in an open relationship, looking for love on an online dating app, or deep into a relationship already — these dating tips and advice are not a one-size-fits-all approach to finding love.

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