Sex & Relationships

Ask Sharleen: I Haven’t Dated in Two Years—Help!

Sharleen Joynt—opera singer, fellow Canuck, former Bachelor contestant and all-around cool girl—answers your most pressing matters of the heart

Sharleen Joynt Flare

(Illustration: Spiros Halaris)

Lower Those Expectations
It’s been more than two years since I ended a six-year relationship because of incompatibility—and I still can’t bring myself to start dating again. Even though I do feel lonely at times, casual sex isn’t an option because it makes me feel terrible afterward. Ultimately, I’d like to enter into another long-term relationship, but I’m terrified of putting myself out there and dealing with all the disappointments and duds. Any tips on how to make the dating experience fun and less intimidating for someone who’s been out of the game?

Sharleen: Girl, you’re in desperate need of a dating pep talk. Look at it this way: a date that’s painstakingly planned and hotly anticipated is often not nearly as much fun as a spontaneous night out sans expectations, right? You’re putting way too much pressure on dating as a whole.

First, the best way to keep dating fun is to view it with a less defeatist outlook. You’re already predicting “disappointments and duds”; what good will that attitude do you? Think more about the possibilities. You could expand your social circle, try a new activity or, at the very least, have an excuse to go to that restaurant you’ve been wanting to visit. Dating is nothing more than getting to know another person. If it leads to a romantic relationship, fantastic. But even if you know in the first five minutes that you’re not attracted, that doesn’t make the other person a dud. Someone’s worth shouldn’t be gauged only by their potential as your partner. Get to know them on a human level.

Second, remind yourself that there are many shades on the spectrum between a long-term relationship (what you had) and casual sex (what you don’t want). Those are not the only options! Your next connection might not become permanent, but that doesn’t mean it’s a failure or not worth your time. Think about what your last relationship taught you, how it shaped the person you’ve become and how you now have a better idea of what you want. I understand wanting what would ultimately become long term, and it certainly makes sense that you shouldn’t be dating anyone
with whom you don’t see that potential. However, to exclusively seek another committed relationship puts a lot of unnecessary pressure on both of you. Instead, enjoy the magic of learning about each other.

Although I’m happy in my relationship, sometimes I honestly miss the getting-to-know-you of dating. It wasn’t about trying to meet my mate. It was about discovering a tiny sliver of the unknown, being social, remaining open to the possibilities—without high expectations. So ditch them and just come as you are. People out there are waiting to be discovered, just like you.

It’s OK to Get Heavy
My mother passed away a few months ago, and it has been extremely tough on me. I just started dating someone new, and it’s going really well, but I’m wondering when it’s appropriate to talk about my mom’s death—beyond the basic facts. I’m very obviously still working through my emotions and will be doing so for a long time. I have a great network of friends, but I also feel like any guy I’m dating needs to know what I’m going through. How soon is too soon?

Sharleen: I am sorry about your mother and commend you for remaining so level-headed and considerate of those around you. Even by asking this question, you’re showing self-awareness and strength in tragedy, which tells me you’re not the type to draw attention to yourself for attention’s sake. This is obviously a heavy topic that you don’t want to broach casually, but it’s possible you’re being too careful. This may sound trite, but when it feels natural to talk about, it is the right time to talk about it. Don’t overthink things. Part of his role as your potential partner is lending an ear (or a shoulder) when and how you need it. If you feel you’ve built a rapport and mutual trust with him—and only the two of you can know if you have—there’s no such thing as “too soon.” Don’t be afraid to be selfish in needing him right now; if he cares for you, he’d have it no other way.

Have a question for Sharleen? Email your queries to with Ask Sharleen in the subject, tweet us @FLAREfashion or post on our Facebook page using #AskSharleen. Then, look for her reply in our April issue!

More Ask Sharleen:
When Does Sharing Become TMI?
My Friend is a Train Wreck, Should I Stop Her?

When Should I Stop Making the Next Move?
My BF Is a Heavy Pot-Smoker, Should I Leave Him?
How Do I Get Back in the Dating Game After Years?
Dating Rich and Ditching the Friend Zone
Why Is My BF Icing Me Out on Social?

And ICYMI, Sharleen is our Bachelor recapper! Read them all now