Ask Sharleen: How Do I Get Back in the Game?

Sharleen Joynt—opera singer, fellow Canuck, former Bachelor contestant and all-around cool girl—answers your most pressing matters of the heart. This month: how to get back in the game and when *not* to get engaged

Sharleen Joynt
sharleen joynt
Ask Sharleen all of your dating dilemmas (Photo: Andrea Joynt)

DIGITALLY DAUNTED

I haven’t dated for seven years. Instead, I’ve spent time with family and friends, gotten my debt in order, travelled and, most importantly, gotten to know myself on a deeper level. Now I’m terrified of putting myself out there. I’m 31 and would like to settle down in the near future; however, I worry that I’m not being open-minded about the new ways of dating. My friends tell me I’m too picky and need to go with the flow, but it’s not in my nature to enjoy online dating. What’s your take on this?

SHARLEEN: I’m going to give you the cold, hard truth. It’s 2015. If you’re not using the Internet to meet a romantic interest, you’re living in the past. I could tell you to join some book club or have a friend set you up, but nothing casts a wide net—which is what you want—like the Internet.

Because I think it’s relevant, I’ll tell you how I met Andy, my fiancé. I happened to sit down next to him at a fundraiser in New York City, and he struck up a conversation. We both knew within five minutes that we had something very special. On the surface, it sounds like your standard meet-cute, but consider this: the reason I was at that fundraiser? I was invited by a guy I had met on Match.com three years prior. We had only gone on one date but had remained friends. As for Andy, he was invited by a girl he’d “swiped right” on Tinder! He never did meet her; he met me instead.

My point? Finding a good match is not about waiting for fate. It’s about being proactive and taking control. Write a witty blurb that expresses who you are, upload honest but flattering photos, and get out there. (Even if you don’t feel like it.) Engage and get to know your date, regardless of whether you’re attracted to him. You may never see each other again, but aim for a nice time with another human being. You never know who you might meet, and you never know who you meet might know.

Related: Try This Sister-Built Dating App When You’re Totally Over Hookups

WAITING FOR A “WHACK ON THE HEAD”

I’ve been dating my boyfriend for five years. He’s much older than I am and was more settled in life when we met. During the course of our relationship, he’s broken up with me a few times for various reasons and then asked to get back together. Now he’s shopping for engagement rings, and I’m really not sure about making that kind of commitment. When the going gets tough, he tends to leave me. But I do love him, and I know what he has to offer. I have a hard time finding a partner who has similar interests, values and priorities as me, which is why I’m still with him. I feel a little stuck because I don’t know if I want to move forward with the relationship, but I also don’t want to end it. I understand that not every relationship is perfect, but mine just seems a little too messed up. I still hope for that whack on the head, the moment when you feel like, oh, now I know. Does that even exist?

SHARLEEN: There are so many things I still need to know! Like, what are the “various reasons” for his breaking up with you? How tough was the going getting? Were they minor spats or an inability to see eye to eye on something major, like money or religion? How many breakups is a “few” breakups?

My biggest questions, however, are: how long have things been going smoothly since the last breakup? (If you’ve been happy clams for years now, one can assume those road bumps are in your past.) And, what was the impetus, if any, for his ring shopping? Did you discuss it with him? Was there an ultimatum involved? Did he have some sort of crisis? Is there a biological-clock factor? I just want to be sure he’s proposing because he wants to spend his life with you, and he’s not using a ring as a band-aid for his past transgressions.

If you’re at the talking marriage stage, breaking up should not be an option. Regardless of the problem, the solution is something you find together; being without the other should not cross your minds. I say this not only because of the times he left you but also because you say you don’t know if you want to move forward.

Please remind yourself that investing five years in someone does not make them right for you. Contentedness and comfort are great, but without trust, they can only get you so far. Ask yourself what you need in your relationship: six-foot-two with a full head of hair? Probably not. Someone who is reliable and will stick with you when things get rocky? Of course. It’s possible he can be that for you, but don’t rush into getting engaged if there isn’t enough evidence of it. An engagement won’t prove his trustworthiness—only time can.

Related: Scaachi Koul on the Realities of Dating an Older Man

Have a question for Sharleen? Email your queries to editor@flare.com, leave a comment below, tweet us @FLAREfashion or post on our Facebook page using #AskSharleen. Then look for her reply in our October issue.

More from Sharleen Joynt:
Ask Sharleen: The Lowdown on Dating Rich and Ditching the Friend Zone
Ask Sharleen: Why Is My BF Icing Me Out on Social?
Read Sharleen’s Bachelorette Recaps

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