Getting Back into the Dating Scene

Welcoming Rejection and Other Approaches

Reentering the dating world after having been partnered for a long time can feel daunting. The world is changing so fast that it can be hard to navigate the new ways of meeting others and the updated rules on how the dating dance works.  Senior sexpert Joan Price has many great suggestions for dating over 60, however, many of her suggestions apply no matter your age.


Philosophy and Approach

The first thing to do is to embrace the process and what it entails. Of course we want it all to work out perfectly and easily on the first go, as it does in Hollywood but rarely is that the reality. So we need to have a positive attitude towards taking a risk and potential rejection. Joan suggests that we actually welcome rejection: she asserts that it saves us a lot of pain and heartache down the line. Of course it can be hard to feel good about ourselves after someone lets us know that we are not right for them. But it is important to remember that this does not mean that we are not date-worthy. It just means that it is not a good fit for them. Having someone let us know early on that they are not interested means that we can move on before we become too invested. Joan suggests, “It gets us one person closer to someone who will work out for us.” And as relationship columnist Dan Savage says, “Every relationship fails until one doesn’t.”

Of course this is also important to bear in mind if you are the one not interested in another. Sometimes we want to spare someone else the pain, but as long as we are clear and sensitive, the best gift we can give another person (as well as ourselves) is to end a connection as soon as we know it is not right.


Meeting People

If you are computer savvy, lots of people use dating sites such as OKCupid, and EHarmony. A quick Google search for specific interests will reveal dating sites that cater to seniors, religious affiliations, specific kinks or interests (eg. nudism or BDSM) and orientations / open relationships. There are even Sexually Transmitted Infection (STI) – status sites where those who are HIV positive or have herpes can find others with the same status. All of these options make it easier to connect with others with similar characteristics.

If it is important to you to find someone whose political affiliations match yours or who is also a bookworm or loves hiking, then consider joining a group or organization with that focus. Try looking for a club in your area. There are a wide variety of groups listed on and you can easily start your own if there is something not already organized in your area according to your interests. While these groups are not designed for dating per se, some feel that a group feels like a more organic, old-fashioned-way to meet all kinds of people, single and partnered, who are interested in similar things. It is not as guaranteed to meet folks interested in dating, but it is a low-pressure environment and regardless, you can do something you love!


Booking a Date

Joan suggests meeting for a short coffee date. You can always extend it if it goes well. Tell a friend where you are going and the date’s profile information. She recommends meeting at 6 pm at a public place that closes at 7. That way, when you are asked to vacate the premises, you can easily head home or, if it feels right, move to another public place that is open. Only meet folks who will send you a photo and make sure that it matches (even if it was taken 20 years ago). If you don’t have a good feeling about someone, trust that instinct. You don’t have to explain yourself.

Take your time and don’t rush into it. Sometimes the slow dance of getting to know each other can be exquisite. When you do make the leap into going to someone’s home, a private space or inviting them to your place, text a friend with the name and address of the person and what time you will check in with them. Set an alarm on your phone for 15 minutes prior to that time to ensure that you do check in with them so as to not leave them hanging. Tell your date that you have to check in with a friend at that time. Anyone who has positive intentions will respect you for knowing how to be safe.  


Practice Safer Sex

It is recommended to use safer sex barriers with everyone every time until you are in a committed (monogamous or poly with clear boundaries and practices) relationship for several months. Joan maintains that if someone wants to have sex with you without protection, that means that they may have done the same with someone else the day or week before, which puts you at an unknown risk. Many folks don’t know they have an STI, as some are asymptomatic. Others won’t tell you that they have one. If you are not used to using condoms on your penis, practice on your own with different brands. They all fit differently and it might take a few to find the best one for you. Pleasure Plus and the Female Condom (also known as the insertive or receptive condom) are especially great for those who have a hard time maintaining an erection with a condom.


The Bottom Line

Put yourself out there. It may be hard to initiate, especially for women who are not usually socialized to do so, but you will learn lots about yourself in the process and perhaps meet some interesting folks. You may not have a great time on each adventure, but Joan’s advice is that (as long as nothing offensive happens) there is no such thing as a bad date, only a good story.

For more suggestions, you can check out Joan Price’s “How the heck do I date at this age?” webinar.

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



Categories: Sexual Health & Wellness