What I Wish I Knew About Dating When I Was Younger

What I Wish I Knew About Dating When I Was Younger

Dating and sexuality can be hard to navigate at any age, but they can be especially hard when you’re first starting out and still figuring out what you are (or aren’t) into. So, we reached out to 22 dating experts, bloggers & matchmakers to give us some insight into their early dating lives with the question, “If you were having a conversation with a young person who had not started dating yet, what would you share with them?” Their answers cover everything from self-confidence to consent and everything in between – check them out below!

Vijaya Chikermane

Executive Director, Alliance for South Asian AIDS Prevention | Twitter

Saying yes to yourself.

I think the most important person you date when you’re young is yourself. It’s when you realize what you like doing, the places you like being, and who you like being with. Sexual exploration is an exciting and important part of this. Knowing what turns you on can help you feel confident about your body and set your physical and emotional boundaries. More than anything, knowing what you like allows you to surround yourself with people who make you happy.

In the midst of all the shame and judgment so many young people feel, especially young women, loving yourself and unapologetically choosing love from others is both bold and necessary.

Elizabeth BrandeisElizabeth Brandeis

Registered midwife and President of the Association of Ontario Midwives | Twitter

As a midwife, I provide information to help the people I work with to make choices that are right for them.

When you’re dating, you have to make a lot of choices, too. Just like choices in health care, different people will make different choices when they’re dating, depending on their own individual needs, desires and feelings.

My advice? Don’t ever feel you have to make a choice just because it was a choice made by someone else you know. Try to make choices that are based on your own desires, feelings and intuition, not based on feelings of obligation or pressure from others. Also, just because you made a choice once doesn’t mean you can’t change your mind.  Whether it’s a choice about who to date, whether to see that person a second or third or hundredth time, whether or not to have sex, whether or not to have sex with other people, make sure you feel those choices are yours.

Some decisions are very hard to make and it’s helpful to find someone you can talk to and count on for information and support. Whether that’s a trusted friend or family member, or a support program like Planned Parenthood or YouthLine, having someone to talk to when you need advice or are making tough choices can really help you feel like you’re not alone.

Carlyle JansenCarlyle Jansen

Owner of Good for Her | Twitter | Facebook | Instagram

If you like someone, ask them out. There are no rules about who can ask whom out on a date.  If someone declines your offer, don’t take it personally. There are many others out there to date. If you are not finding people you connect with at school or work, do activities that reflect your values and interests to meet like-minded folks: a sport, a political/environmental/cultural group, a hobby or other activity you enjoy.

Go slowly. If you like them and they like you, there will be a next time when you can take another step.  Don’t be rushed by someone else or compromise your needs and boundaries for their affection or  attention. Sometimes you don’t know you have hit a boundary until you have gone past it. It is way easier to recover from a boundary you realize was crossed by a little than by a lot.

Take care of yourself. From where you meet, to making sure that someone else knows where you are and with whom, from asking for consent to obtaining, discussing and using whatever safer sex products are the best choice for you. If someone puts you down or suggests that there is something wrong with you, listen to your gut and find someone else to date who makes you feel awesome about yourself. You are worth it!

There are no right or wrongs when it comes to dating. Each situation is different. Talk to friends or adults with similar values about what they have learned in their experience, read about dating from other youth at places like Planned Parenthood Toronto, scarleteen.com, sexetc.org or books like The Little Black Book for Boyz/Girls written by other youth in Toronto. Follow your head as well as your heart. Focus on yourself and what you want to do and don’t worry about what others are or are not doing.  You will have some fun times and will learn as you go. We all made choices that we realize weren’t the best. Go easy on yourself if you make what you consider a mistake. If you think that something not quite right happened, talk about it with a counsellor or trusted friend or adult. They can help you figure it out.

Ama ScriverAmanda (Ama) Scriver

Freelance writer | Website | Twitter | Instagram

Okay so here’s the thing – dating is complicated but it’s a lot of fun for so many different reasons. It’s not just who you will date or the people you will meet, but the experiences you will have. One of the things to remember is that while dating can be a lot of fun, don’t feel forced to do it, or to move into anything you don’t feel comfortable with – sexually or otherwise. Always make sure you’re in a relationship that makes you feel safe (mentally, emotionally and physically) and secure. Don’t be afraid to stand up for yourself – good relationships are built on being assertive. Okay so now that I’ve said all this – yes I absolutely promise that dating is fun! Just take it slow and see what happens.

Charlotte Henderson

Outreach at Come As You Are | Twitter | Facebook | Instagram

Great question! I think what I would tell a young person who hasn’t yet started dating is something I tell lots of adults, including myself, all the time, which is to work at enjoying your body. Both in terms of feeling good in your body, and knowing what makes your body feel good. Because we all get a lot of messages that our bodies could be better, and that they should work a certain way. And it’s crap. And it gets in the way of really enjoying relationships and intimacy.

I would say, It’s hard for us to feel pleasure when we feel unhappy or ashamed of our bodies. So as much as you can, surround yourself with people, and books, and movies, and images, and organizations, that make you feel good about yourself in your body. That person who you really admire, make them your screensaver! Look in the mirror and find something you really dig about yourself and celebrate it, then let the list of those things grow! It’s ok if it feels hard, it is hard, so try to be patient with yourself.

The second part is figuring out what makes your body feel good. Because your body isn’t going to work exactly like anyone else’s. This is why Cosmo’s sex tips can be fun and/or hilarious but aren’t usually that helpful. Find out what feels good to you. Pay attention to how your body feels when you feel happy, or sexy, and how it is different from when you feel nervous, or scared. The better you know your body, the easier it is to enjoy exploring it with someone else! Lastly, don’t worry if you don’t feel like you have it all figured out right away, nobody does!

GUTS Magazine Editorial TeamGUTS Magazine Editorial Team

GUTS Magazine | Twitter | Facebook | Instagram

All relationships, whether they’re with friends, crushes, people you have sex with, or people you date, take work. All of them are equally valid to be working on, and you’re the best expert at figuring out 1) what kind of work works best for you and 2) what kind of people you want to do work with.

The world puts a lot of pressure on people to be in a couple, and it’s ok not to be in one! It’s ok not to date! Your friends might be just as important as any boyfriend/girlfriend/person you want to fool around with. Go at your own pace. Be gentle with yourself. Listen to this Carly Rae Jepsen song.

And importantly: nothing you do makes it acceptable for people to not respect your boundaries.

Sofi PapamarkoSofi P. Yenta

Friend of a Friend Matchmaking

I would tell myself, and any hopelessly optimistic and romantic young lady, to never believe a word a dude says when he’s got an erection. Seriously! I know they never meant to hurt me and maybe they 100% meant what they said in the heat of the moment, but any “I love you”s or “I want to be with you”s or “I’m breaking up with my girlfriend for you”s are officially null and void when uttered by a dude with a hard-on. That simple truth would have saved me a lot of heartache, I think. Take into account his words and actions and treatment of you (excellent, I hope!) in your regular day-to-day life.

Caitlin RobertsCaitlin K. Roberts

tobeaslut.com | Twitter | Facebook

Your body is capable of experiencing pleasure; this pleasure is essential to your mental, emotional, spiritual and physical well-being. You are not a prop or a presentation, your validation exists in the way you move within the world, not how many boys think you are “sexy”. Your sexual power and prowess will come from a deep, deep sense of knowing who you are, recognizing when to speak up for yourself, and unlearning all the shit that popular culture has fed you and sowing the seeds of your choosing where they failed. Read and question everything. You are already powerful.

June MorrowJune Morrow

The Change Room | Twitter

1. You don’t have to have sex with a guy to make him your boyfriend.

I was very promiscuous in high school. I liked sex and I liked the way it felt when I got that kind of attention from a guy. I thought at the time if I liked someone and wanted them to like me back, the best way to win them over was to have sex or do something sexual with them (after all, all boys want sex, right?). Turns out I was wrong. What I didn’t realize is that sex could be the icing on the cake of a good relationship with someone and that a lot of boys were actually okay with taking it slow.  

What I know now that I didn’t know then is that a real relationship is about more than just feeling good, physically. It’s about being friends and supporting each other and doing non-sexual things together. When you wait, it allows a guy to see your other great qualities, and when he sees these and likes them he will go out of his way to try to prove himself to you (which is a really nice feeling). Waiting also allows you to make sure he’s really worth it (beyond simply being cute), which prevents you from sleeping with losers who you originally thought were winners.

2. Never, ever let anyone define your self-worth based on your sexual activities.

Because I had so much sex and wasn’t shy about it, I developed a reputation in high school as a slut. Eventually, I was bullied and ostracized by my peers (at one point someone threw a brick through my bedroom window with the word SLUT written on it). I felt worthless and became depressed and suicidal. Ultimately, I had to get therapy and change schools.  

I let the haters get me down.

What I know now is that those bullies were simply afraid. There was something about my sexual behaviour that threatened them and made them act the way they did but their actions weren’t about me at all. It was about them and their fear of a form of sexual behaviour that was different than what they were comfortable with. None of this was about my value as a person or even if what I was doing was right or wrong. They were ultimately just frightened little kids acting out.  

If I could go back in time, I would ignore the bullies and really focus on all of the good things in my life. Because here is the thing: there were kids in my school and neighbourhood who despite my reputation still wanted to be my friend. There were people who knew that the real me was creative and smart and talented and capable of so much more than what the bullies wanted me to believe. I ignored these people because they weren’t the kids whose approval I desperately wanted. But, in retrospect, I clearly see those were the kids I should have hung around with more.

If you’re being judged or shamed by other kids, find people who judge you on your character, not on what you do or don’t do sexually with others. Those are the people you want to be your friends.

Ignore the haters unless they are doing something illegal like sharing a sexual image of you (or throwing bricks through your window). In that case involve the police and press charges if possible. Seriously, do it. It will help you reclaim your power.

Finally know this, middle school ends, high school ends, reputations fade, people get on with their lives. What seems like a huge deal now is simply a blip in your life. Keep it in perspective and above all never let anyone else define your own self-worth – especially not based on your sexuality or sexual activities, which frankly is no one else’s business but you and your partner or partners’.

Karen ChanKaren B K Chan

Fluid Exchange | Twitter

You have the permission to feel all kinds of things. To want, to not want, to question, to be ambivalent. Dating is one way of engaging with the world, with people, and with yourself. All your shit comes out when you’re getting near someone else, especially if desires and romance and sexuality are involved. I’d say that for me, dating has been best experienced as experiments, as curiosity chambers. It’s not just a search for other people. It’s a trying out of different selves. Who do i want to be? Do i like this person? Who else could I be? What am I learning?

Shit is scary. Being close to someone else is scary. Hoping for certain outcomes is scary. Rejection is hard (and real, and necessary, and it’s supposed to happen to you). So all of that takes courage. Just because it’s hard doesn’t mean you’re doing it wrong. It’s in perfect balance to how amazing it can be too, and that takes courage too;, to seek, to recognize it when it’s there, to accept and receive and let yourself be known.

Wisdom is just perspective. To know that the first year of your dating “career” is going to be very different from your 5th, or 10th, or 47th. Patterns reveal themselves (in other people, in ourselves) over time, and it does take time, and all that is left is ever-growing wisdom. One thing that i work really hard on, is to stay open and stay soft. It can be hard to survive through hurt and loss, to lose hope and find it growing again, to feel weary from betrayal or to tire of your own shit. All of that is good and ok, even the shitty moments. The thing I try not to do is to become hardened by pain and fear; not to play it all like a game I want to win; not to get mean or cold as protection. Because when I do that I lose the ability to really connect, to let magic appear between someone else and me, and then people really do suck.

I guess it’s quite cliche to say, but I really do believe it. For really amazing connections — be that with a date or lover or partner or a friend — you have to be you. You have to offer some kind of genuine, imperfect self, so that it’s available for other people to connect with. For some of us that’s easy, for most of us it is the hardest thing and it takes decades to learn how to really truly be real. But you know, it’s one of the truest things I know; that I have to be in the room to “find” true love, and I  mean that in a wide, encompassing way, beyond romance and sexual partners and all that. True love is the kind of connection that truly eases loneliness. It’s the bestest stuff that keeps people safe and warm, and it’s both ironic and rightful that we have to take such risks in order to create it.

Nicole McCanceNicole McCance

Nicole McCance Psychology | Twitter | Facebook | LinkedIn

Going on dates doesn’t necessarily mean having sex. Before starting to date and getting caught up in the whirlwind of emotions that come with it, take some time to think about what you want the experience to be like. Dating should be fun, where you feel great about yourself as you learn about the other person. If you do want to have sex, plan ahead. Be ready for this important decision. You may want to have condoms with you and even think about whether you want to go on birth control beforehand. This way you can better enjoy the experience of dating. Overall,  always listen to your gut and chat with good friends for guidance when you feel lost.

Jessica Louise LiJessica Louise Li

www.JessicaLouiseLi.com | Twitter | Facebook | LinkedIn

I know you may wonder if you’re beautiful and if any boys will even want to be your boyfriend. It may seem that you need to dress sexy and have your makeup and hair all nice to attract boys. But all of those things don’t really matter at the end of the day. You deserve someone who will respect you for your own uniqueness and that, my beautiful one, is someone who is deserving of your body. Honour your body for it really is your t-e-m-p-l-e, even if that seems cliche. It’s the gift you have in this life to experience everything so treat it with respect. Boys are horny and always want to touch and grab you but they really don’t know how powerful and wise you are! Enjoy life by doing things that make you happy and you WILL attract a guy worthy enough to be in your presence. Trust me, I found him.

Jenna NakamuraJenna Nakamura

The Sex Dojo | Twitter | Facebook

Think about why you want to start dating. Is it because all your friends are and you think you’re supposed to at this age? Do you have someone you like and want to spend time with them/have a relationship? You need to think about and talk to your family about their values around dating (ie – does the family say no dating until a certain age or point in their life, is their family okay if they start dating?). What does dating mean to you? Is it hanging out together at school, outside of school? What activities (perhaps sexual) does that include and what are you okay/not okay with?. There is no right age for someone to start dating. A person needs to ask themselves/find answers to the above to know if they are ready to start dating.

You  will get rejected at some point in your dating life and that it is okay. It might hurt for a little but it’s temporary. You need to be okay with hearing ‘no’ or that someone doesn’t like you, or want to date you. People like people for different reasons and not everyone we like will like us back.

Most importantly, consent is a MUST when you start dating. You need to get consent whenever you are doing a sexual activity. Consent can be taken away at anytime. Just because you started doing a sexual activity doesn’t mean you have to continue. Consent is ongoing and understanding that it can be taken away at any time, and needs to be respected by your partner is very powerful.

Natasha SharmaNatasha Sharma

NKS Therapy | Twitter | Facebook

Dating is healthy and can be fun! However it can also result in feelings that make us behave in ways that resemble socially-acceptable insanity. If you decide to date, be mindful in who you pick! Date someone if you thoroughly like that someone. Don’t date just for the sake of dating; there’s nothing you are supposed to be doing in life – ever. There’s a difference between “dating” and being “in a relationship.” Make sure you’re not “dating” someone who wants a relationship, or that you’re not “in a relationship” with someone who is “dating” you. Finally, if you’re sexually intimate with your special “other”, be prudent, safe, and plan for what you want – or don’t want – at whatever stage you’re at in life.

Kavita DograKavita Dogra

We Talk Women | Twitter | Facebook

It’s going to be like riding a roller coaster. Dating is fun, emotional, hilarious, awkward, exciting and you ought to embrace all of these emotions in order to learn from the people or person that you date. Be grateful for the people you meet and the lessons they teach you, don’t waste time on regrets. Never compromise on your values. Relationships are about give and take, but don’t change who you are as a person. If you do, you’ll never be happy. Stay true to your evolving self, respect yourself and most importantly love yourself. Know that you are worthy of love and respect, because you are. Violence and abuse in any form are unacceptable but if they occur don’t blame yourself or feel ashamed. Seek help and support. The good, the bad and the ugly; enjoy it.  

Kim and Amy SedgwickKim & Amy Sedgwick

Red Tent Sisters | Twitter | Facebook | Instagram

This is the perfect time for self-exploration! If you learn about yourself and what turns you on (and what turns you off) now, you’ll be better equipped to communicate those desires to a future partner. Plus, it’s a great opportunity to think about what kinds of values are important to you in a relationship e.g., trust, honesty, communication. That way, when you begin to date, if someone isn’t able to offer you the kind of partnership you need, you will be able to recognize that quickly and move on to someone who can. Lastly, knowledge is power!  We can’t expect to be good at something we’ve never been taught and unfortunately most of us don’t receive comprehensive sex education. So take matters into your own hands and check out resources like Scarleteen. That way, you’ll be armed with everything you need to know to confidently explore your sexuality and build a healthy relationship with yourself and a partner.

Soha KareemSoha Kareem

Diversity & Inclusion Manager, Riot Games | Twitter | Instagram

If the person you’re with tries to guilt trip you into any sexual activities, walk away from them fast and early. Manipulation is not, never has been, and never will be consent! The folks with which you develop healthy sexual relationships will always understand when boundaries are crossed, and they will do their best to never cross those boundaries again. Stay open, honest, and don’t be afraid to ask for what you want and stand for what you don’t. You got this!

spot-of-delightA Spot of Delight

Spot of Delight | Twitter | Facebook

Dating looks different for everyone. Hopefully you’re entering a relationship because it’s something you WANT to do, and not because you feel is expected of you. Relationships are supposed to be fun – not a status symbol or method of proving something. You have the right to set your own boundaries – and the duty to respect those of your partner. Talk to each other; learn what they’re ok with doing and what they aren’t, and don’t be afraid to voice what YOU may be ready for and what you’re not. Communication is key. Of course, this does not mean that if they agree they’d be interested in trying something in the future, that consent can be implied when the time comes. Consent is an ongoing process. Informed and enthusiastic consent = less chance for miscommunication.  

If you both decide that getting physically intimate is something you want, have a conversation about safer sex (whatever applies). Does that mean talking about condoms? Dental dams? Oral contraception? Sexual history (and have they been tested before)? Just because these healthy conversation points aren’t represented in the movies and tv shows we watch, doesn’t mean they’re not real-world conversation that need to be had. No relationship is perfect – but communication and mutual respect can help! Above all, Spot of Delight supports your right to choose! We hope that your choices feel empowering and honour your rights and needs. Please know that you can talk to us at any time.

Harris O'MalleyHarris O’Malley

Dr. Nerd Love | Twitter | Facebook

The first is to be honest. Be honest with the people you’re interested in – don’t beat around the bush or hide the fact that you’re interested in them by trying to be friends. Being up front about liking someone and the kind of relationship you want is important for the both of you. It’ll help you avoid a lot of heartache later on. Also be honest with *yourself*  about the kind of people you would want to date and the people you’re attracted to. There’s a LOT of pressure to only be into a certain body type or type of person, even if you’re attracted to someone completely different. Being honest with who you actually want to date instead of who you *should* want to date will make you *and* your dates happier in the long run.

The second is all about consent. You don’t want to focus on someone saying “no”, whether it’s to a date, to a kiss or to sex – you want to get a clear and enthusiastic “yes”. You want somebody who is as into what you want to do as you are, not somebody who’s feeling pressured into doing something they don’t want or isn’t comfortable with something but will put up with it or is giving in because you won’t stop bothering them. Getting that happy, enthusiastic “yes” means you’re both on the same page, that you want the same things and you’re both ready.

Cynthia LoystCynthia Loyst

Find Your Pleasure | Twitter | Facebook

I know you’re feeling a lot of pressure and expectation about the “first time” but I’m here to tell you that it’s not necessarily going to be accompanied by roses or fireworks or sunsets. That’s a mythology that Hollywood and romance novels have created.  The good news is virginity loss doesn’t have to be a single moment by which the rest of your sexual life is defined.  The truth is that there will be many firsts throughout your sexual life. Think of sex like a buffet where intercourse is only one course that you may or may not choose to put on your plate.  

So instead of focusing on the first time, focus instead on pleasure. Ask yourself questions like: does this feel good?  How can we make it better?  Do I feel physically and psychologically safe? And don’t be afraid to communicate with your partner – there’s no point in moving forward if you aren’t feeling great about things at any stage.  

With that in mind, before exploring someone else’s body, make sure you know your own really well first. You can be your first (and often, best) lover in life.

Stephanie DavidsonSteph Davidson

Steph Not Stephanie | Twitter | Instagram

I thought long and hard about what I’d say to my younger self, before I got involved in the sometimes messy business of sex. There are areas in life where I’d love to go back in time and gently guide less-experienced Steph in a different, perhaps kinder direction. My sex life though? It’s not one of them. While there are experiences (and people) I wouldn’t repeat if I had a chance, there’s nothing so bad I would take it back. Sure there are plenty of cringe-worthy memories (the penis was a bit mystifying when I first encountered it) and more than a little heartbreak because sex is messy, but these are the things that shaped me into who I am today—sexually confident, proudly feminist, open and accepting, and hopefully empathetic. So rather than advice, I just have this to tell myself: Get it, girl.  

Jennifer DecanJennifer Decan

Jenn and the City | Twitter | FacebookInstagram | Snapchat | YouTube | Pinterest

Slow down. Slow down, and before you even begin to think about allowing someone else to love you – love yourself.

Love yourself enough to know that your validation and worthiness does not stem from the attention you are so eagerly seeking. All these boys you think are ‘oh-so-cute,’ and are ‘in love’ with, trust me – there will be plenty of that in the years to come.

Love yourself enough to know that what you’re feeling is normal. It’s normal to be scared; it’s normal to question yourself. It’s also normal to have urges and desires. It’s normal to want to try different things – but never, ever let someone else pressure you into doing something you are not comfortable with or ready for.

Throughout life you will be faced with challenges and opportunities, and it is up to you to realize that the decisions you make today will affect your life from that point forward. No matter how insignificant they may seem at the time – they will, I promise you that.

So slow down, because there is absolutely no need to rush into anything.