Further Discourse on Dating:

Part II of Dating In the Modern Age

Last month this column discussed online dating. This month’s article follows up on the topic to address some dating ideas in general. Like many things in life, much of what follows is common sense. However sometimes we need reminders to make sure that we put good protocols into practice. You might also learn a tip or two to make dating more fun, fulfilling or successful for you.


What are your goals?

Luna Matatas, pleasure coach at LunaMatatas.com recommends thinking about your goals of dating. What are the types of experiences that you want when you are dating: food, theatre, exploring, intellectual conversation, an escape from work? Then write out a checklist for who you are looking for: are you interested in someone who wants to experience the same new activities? Do you want a more casual or committed sexual connection? Are you looking for affection or just passion? Do children appear in your future and/ or are you open to dating someone who already has kids? Luna also recommends getting clear on what you are also not looking for in your search.


Build Your Confidence

Luna recommends taking stock of yourself in terms of what you have to offer. What are you gifting someone on a date? What are your dating assets? It is important to start from a place of confidence in yourself as someone with lots to offer rather than in desperation. Do what you can to make your life on your own the best it can be. You are better off on your own than with someone who does not enhance your life. If you are shy about flirting, Luna suggests pumping yourself up beforehand by wearing something that you feel confident in (even if the confidence- enhancing clothing is hidden). Practice smiling at yourself in the mirror and do something that helps you to relax. Even self-pleasure can be helpful to rid yourself of tension. While on your date make eye contact, smile, and be genuine with your body language. Take deep breaths if you are nervous.The more confident you feel, the less likely you are to settle for someone who is not a good fit just to fill a void inside.



If you are posting a photo online, Luna emphasizes not to use a group photo, but instead to use a full-body image. This shows confidence and authenticity. Don’t cover your face with sunglasses, a hat and/ or hair. If you have activity photos, put them in the mix rather than as the primary photo. It is great to show your personality but people want to see what you look like. Make sure that your photo was taken within the last 6 months, and don’t just pull one at random from your facebook profile. Be deliberate with how you want to present yourself.


Get creative

The ideal first date is for a quick beverage. If there is chemistry, then you can decide what you want to do the next time. Luna recommends considering your interests when planning a follow-up date: going to a used bookstore, taking a walk in the park, visiting a museum or art gallery, or taking in a festival. Check out the local listings on events websites such as BlogTO.com for inspiration. Taking in something to discuss together generates better fodder for conversation, since it can be awkward at the beginning. It can be easier, more interesting and more revealing about your date’s values and priorities to have a shared experience to discuss rather than talking about your separate lives.


Discussion Topics

Speaking of conversation, keeping dialogue interesting on a date can feel like as much pressure as a job interview. The number one rule is to not dwell on past relationships. Luna asserts that blaming an ex-partner for a miserable relationship does not make you look good. When discussing your past relationship history, make sure that you also talk about your own mistakes and what you learned as long as it is light. Showing that you can be self-reflective, take responsibility, and be open about yourself are attractive characteristics. Balance discussing your strengths with your learning edges. Both arrogance as well as self-deprecation are unappealing traits to most.  


If you are passionate about your work, then share that enthusiasm. But Luna advises that it is hard for someone else to get into the conversation if you go into too much detail or complain in depth about your work or employer. You want to always give your date something that they can engage with. She suggests that you lead with topics in the direction of your goals. For example, if you are really passionate about intense subjects like politics or religion then by all means bring them up and gauge your compatibility on those topics. Otherwise focus on topics that are more connected to your values. Luna advises not to give everything away at once though: it can feel like an emotional dump for your date. She elaborates that dating is about uncovering mystery. Sharing of deeper aspects of yourself is more valued after you have built more respect, connection and trust over time.  Create some mystery for your date to get to know you better and learn what is under the surface of who you are.


Always remember that we sometimes have to meet a lot of people before we find someone who clicks with us. When someone declines a second or subsequent date, it does not mean that you are not datable; it is just that you are not the right one for that specific person. If you are going on lots of dates and not finding people who are a good match for you, get a friend to give you honest feedback about your dating profile. Perhaps they will see that who you claim you are looking for is actually not who you want to date. It is a good idea to review your priorities and vision periodically anyhow. Is it realistic that the person you are looking for exists? If you are constantly disappointed by the fifth date, perhaps you are not screening well enough at the beginning? Look for patterns and re-assess what your strategy is. In the meantime, keep cultivating a fabulous life as a single person, doing the things that you love. Sometimes Murphy’s Law (and romance novels) dictate that when we are happiest on our own and not looking for love, that this is when the right person finds us and takes us by surprise.


Carlyle Jansen is the founder of Good For Her, a sexuality shop and workshop centre in Toronto. If you have questions or comments, email carlyle@goodforher.com or go online to goodforher.com




Categories: Sexual Health & Wellness