Ask Sharleen: When Should I Stop Making the Next Move?

Sharleen Joynt—opera singer, fellow Canuck, former Bachelor contestant and all-around cool girl—answers your most pressing matters of the heart. This month: whether to make the first move and what to do when he won’t say what you need to hear

Sharleen Joynt
sharleen joynt flare
(Illustration: Spiros Halaris)

Out Of Reach
I’m in my mid-30s and live in a huge city. I’ve been dating online for three years now and though I hate it, I continually force myself to put myself out there. I always struggle with whether to contact a guy after going on a couple of dates (which seem to go well) and then not hearing from him. In my experience, if a guy is really into me, he’ll generally make the first move to follow up. I know a guy has lost interest the minute his communication “breaks pattern.” I’ve been on 30 to 40 first dates in the past three years, some of which went on to three to five more dates. If I really like a guy, and he suddenly doesn’t follow up anymore, I reach out. But only twice have I ended up seeing the guy again. The rest of the time, I hear nothing back. And it’s incredibly sucky. Guys always say that girls should wait for the guy to make a move—if he’s into you, he’ll make it known. So should I stop reaching out?

Sharleen: The problem with Internet dating, as wonderful as it is in terms of expanding our selection of prospects, is the age-old paradox of choice. There’s a bit of a grass-is-greener epidemic, especially in larger cities where there are so many options. It’s for that very reason that you shouldn’t take any of it personally. It has less to do with you—especially if you’re reaching three to five dates with the same person—and more to do with too many people wondering if there’s something better around the corner.

I’m a bit of a traditionalist in that I believe men like to pursue. When women take the reins early on, they’re too easily labelled desperate. (I’m not saying they are, but it’s an unfortunate corollary in our dating day and age.) So, yes, after the first date, I do think a woman should sit back and let the man initiate contact. (I feel the opposite leading up to the first date, but that’s a topic for another day.) I say this not because I think women should wait to be chosen, since of course you are choosing him as much as he’s choosing you. But a man’s initiative in the early stages of dating says so much about him: Is he quietly confident or completely arrogant? How is his ability to plan, commit to those plans and make decisions? Let him give you that data so you’re the one doing the choosing. If he doesn’t reach out after the first date, that’s information. If he fades away after a few outings, that’s great information. Better to learn this after five dates than five years.

Lastly, you know the saying, “If it ain’t broke, don’t fix it”? After three years of dating and 30 to 40 first dates, it can’t hurt to examine your own patterns. What sort of men are you repeatedly going for? Your match may not come in the package you think. He may be a different age or not look like what you’d envisioned, but those things don’t matter if he makes you happy. So let that paradox of choice be your problem. Open your mind to the abundance—and diversity—of options out there; you may discover someone you would have originally passed over.

No Words
My boyfriend and I met in college, and we’ve been dating for a little over three years. We frequently discuss our future and know that one day we want to get married, have kids and grow old together. He’s a hand holder, forehead kisser and champion cuddler, yet whenever I need him to tell me how he feels, he changes the topic. He says he dislikes discussing his emotions and that it’s just his personality. Whenever I press further, he typically shuts down or gives a half-joking leave-me-alone groan. I truly believe actions speak louder than words, but sometimes a girl needs to actually hear that her guy is nuts about her. Should I be concerned?

Sharleen: Uh-oh, a discrepancy in the infamous Love Languages (the bestselling relationship tome from the ’90s that was republished earlier this year). I have been in your exact position before, with the same gripe, and it’s tough. You don’t want to feel like you have to fish for affectionate words, but you don’t know how else to get them.

You need to tell your BF how important it is for you to hear how he feels. It’s not about pressing—it’s about clarifying. If he’s a true “actions speak louder than words” guy, he’ll listen and implement that information in little ways as best he can. It might not be easy for him; effusion doesn’t come naturally to some people. But just as I’m sure you make the effort to express your feelings for him in the ways he understands, he should learn your language. If he listens but makes zero effort, there’s a bigger problem here.

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 an upcoming issue.

More from Sharleen Joynt:
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?

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