Our Ultimate Guide to Dating

Learn all you need to know about how to date.

Dating is not an easy game to play for our generation. From sliding into DMs to steering around hook-ups to wondering how much to drink on a first date, there are a thousand questions to answer just to muster up the courage to ask someone out.

Well, we’re here to answer some of them. Here’s a collection of our best dating advice.

Make the most of being single

You’re here for the low-down on dating, but don’t be quick to rush past the gifts of being single. Everyone has a desire to be deeply known and loved, but finding a romantic partner won’t magically make your life complete. In fact, being in a relationship isn’t an automatic cure for loneliness for single people

So while you’re wading into the dating pool, it’s worth it to learn how to enjoy being single by taking advantage of the space you wouldn’t have in a relationship. It’s a great time of your life to travel, develop a hobby, give your time to others, and learn more about your own personality. Discover how to be happy single and you’ll develop important habits and dispositions that actually increase your capacity to engage in a meaningful romantic relationship should one emerge down the road. 

And while you wait for Mr. or Ms. Right to cross your path, it’s not easy to figure out how to be patient in love. Here are important insights to remember:

  • You’re not incomplete.
  • Nobody is going to show up and make you feel more confident, attractive, or worthy.
  • Your life is meaningful just the way it is.
  • Everybody loses when you act out of impatience.
  • Life is a mystery, and no matter what you do, you never know how or when you might meet someone.

A roadmap for the dating journey

We’ve had a lot of writers share the lessons they’ve learned in their romantic journey, and their hard-earned wisdom can help you get your head on straight before you get in the game, especially if you’re feeling afraid of dating

For example, these dos and don’ts of dating can keep you grounded:

  • DO be yourself; be honest; be generous.
  • DON’T date if you’re not ready to date; don’t be blinded by beauty; don’t introduce physical affection too soon.

It’s important to acknowledge the hookup culture that can shape expectations around dating encounters — and the dangerous ways it objectifies romantic partners. In fact, being thoughtful about the role of physical intimacy can keep you anchored to seeing someone’s beauty as more than skin-deep (which is why it’s worth it to ask, Why is chastity important?).Taking a step back to ask “What is true love?” in the first place can help you reframe your expectations and set a high standard for what you want to find in dating. 

Stepping outside of yourself can help you find perspective. “The Dating Project” is a documentary on modern dating that has real lessons to offer about what makes dating unique at this moment in history. And don’t forget you have friends among Catholic saints for love: they experienced all the highs and lows of romantic emotions, too, and found a way to remain true to themselves through it all. 

Finding someone to date

Whether you’re coming out of a pandemic or a breakup, learning how to start dating again isn’t easy. But there’s no rush! Remember: time is your friend, work on being present and outward-focused, and know who you are. 

If you are ready to start sliding into DMs, here are some tips:

  • Social media apps are the new dating apps: Social platforms lend themselves to conversations, which makes it easier to have an exchange with someone you’re interested in. 
  • It’s less scary the more you do it.
  • Cast a wide net: Expect a lack of replies, but don’t let that discourage you.
  • Messages can determine compatibility: It doesn’t take long to get a read on someone when you’re having a conversation, even digitally. 
  • Leave it if “left on read” — if they’ve moved on, so should you.
  • Never take it personally: There are hundreds of reasons a connection might fall apart — don’t read too much into it. 

And if all that fails, it’s actually not a terrible idea to think about family set ups. For one, your family knows you better than anyone else, so there’s a good chance your values will align with the person they see for you. And second, that first encounter will be more organic than a meeting you arrange through an abstract, digital exchange — right off the bat, you’ll have something to talk about with each other. 

Online Dating

If the DM-method or family set ups don’t do the trick, there’s always dating apps. But does online dating work? There are several indications it does:

Does online dating work? This author shares 3 reasons why he's still using dating apps.

Even beyond the numbers, there are great stories of people searching for someone and finding love in the digital jungle. Reading between the lines of an online dating success story here and there might help you see what works and what doesn’t in this medium. For example, it might just be a good idea to step outside of the reigning norms to find your own path. 

If you’re ready to get into some nitty gritty online dating tips, remember to engage these platforms with intentionality. And it’s helpful to lower the stakes as you start. Here are three fundamental dating app tips for bringing your romantic quest online:

  • State your intention upfront.
  • Keep it real and do what you love.
  • When it’s over, end it promptly. 

If you’re looking for rules of the road to guide your way with a dating app, we have you covered, too. This writer leads marriage preparation sessions, so he’s heard many stories about what works (and what doesn’t) in initial encounters that grow into something promising. His suggestions for online dating etiquette include:

  • Be not afraid.
  • Be authentic.
  • Be outgoing.
  • Be responsive.
  • Be realistic, not desperate.
  • Be chill.

Going out on a date

Finding someone to date is one thing. Knowing where to go and what to do on a date is another. 

The first task is asking someone out — when that special someone catches your eye, how do you break the ice? This writer has patented his own “three-step plan for asking someone out on a date”:

  1. Start a conversation.
  2. Continue the conversation.
  3. Ask to be in touch.

One of our writers found a surprising source for dating skills in her experience doing improv. The responsive listening and creativity from that brand of humor helped her get over awkwardness on first dates. And make no mistake, dating is a skill — and one you can get better at. You can even prepare ahead of time by having in mind topics to address on a first date

If you feel like a dating partner has potential, here’s some solid flirting advice: sustain eye contact, be generous with compliments, and aim for honesty and vulnerability to move things forward. Be careful when dating and drinking — if you can’t date without getting sloppy, something’s not quite right. Best to make a plan ahead of time for how much you intend to drink on a date. And if you’re into sober dating, you’ll be in an even better position to have conversations of depth.

So, what should you invite your new date out to do? There are a million summer date ideas, from going to a ballgame to going for a walk or ride to exploring a new community festival together. And if you’re looking for less adventurous (but more intimate) options, at home date night ideas can range from a hot sauce challenge to streaming comedy shows to a DIY bake-off. 

The most important thing to remember on a date, however, is being authentic: attend to the thoughts and feelings you’re having around this dating experience. Those interior cues will help you see a way forward in this relationship, and will keep you centered if your heart gets broken. 

Dating + managing mental health

Many people are under the impression that dealing with anxiety or depression disqualifies you from the dating scene, but this isn’t true — it just takes some extra care to manage a healthy approach to both areas of your life. 

If you’re dating with anxiety, remember to put your mental health first. And practice conversing with strangers — going on more first dates will put you at ease. If you’re not seeing positive developments, don’t forget to give yourself credit for the effort it takes to get out there.

If you’re dating with depression, make sure you take care of yourself and are aware of when you’re ready to date. Perhaps it goes without saying, but your partner should be a positive, supportive person. Because exercise plays a key role in managing depression, doing something that involves physical exertion is a great outing.

On the other hand, if you are dating someone else who is managing their mental health, you may be wondering how to support them, and how to avoid patterns or contexts that might pose a challenge for them. 

If you are dating someone with anxiety, it’s important to remember that they can’t just “snap out of it.” And you don’t need to fix them — it’s enough to learn their coping techniques (and support them) and be aware of your own limitations. Clear communication is always important in relationships, but especially so in this context. 

If you’re dating someone with depression, just know that the experience is real, and might last a long time. Exercising together is helpful, but even more important is your honesty. If they seem distant, you might consider helping them find professional help.

The end of the road

Not every relationship has what it takes — and that’s okay! Dating is a process. It’s nothing more than a way to encounter many different people who are probably looking for many different things. It’s not realistic to expect to find a lifelong partner on your first date. 

So then the question becomes: Should we break up or stay together? There are many different signs that might be pointing toward the exit ramp. One is that you might be dating potential instead of a person — that’s a cycle you’ll want to name and address right away if you notice it within yourself. 

If it’s time to throw in the towel, here are some tips on how to break up with someone nicely:

  • Communicate directly and be straightforward.
  • Don’t use a line — speak the truth in your own words.
  • Remember that your soon-to-be ex is a person with dignity. 

If you find yourself on the other side of the equation and your romantic partner is breaking off the relationship, you know all too well the pain of heartbreak, whether you’ve been ghosted or the other person had the decency to speak with you directly. Either way, take a deep breath — this isn’t the end of the world. Remember what you can (and can’t) control, and seek better self-awareness. Here are some insights on how to survive a breakup:

  • Don’t react immediately.
  • Give it some time.
  • Expect your emotions to be conflicted.
  • Surround yourself with a supportive network. 

Breaking up is hard, but it’s a step toward greater growth. When we spoke with a range of people about what they learned from failed relationships, they had a lot of wisdom to share: 

Grotto quote graphic about lessons from failed relationships: "1. Don't forget your own worth; 2. listen to your gut; 3. your fulfillment doesn't come from your significant other; 4. don't stay because you're comfortable or idealizing; 5. Don't dwell on your exes' flaws; 6. pain is necessary for growth; 7. see the person first, not your expectations; 8. you can't force love."

And don’t give up! Just because this relationship didn’t work out doesn’t mean that you won’t find love after heartbreak. As the saying goes, there are a lot of fish in the sea — don’t lose hope!

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