3 good reasons to make the first move

By Theo Pauline Nestor

When my friend Stuart was a teenager, he and his friend were on a mission to find some fireworks. They stumbled into a convenience store where Stuart found himself face to face with a young and attractive clerk. Stuart then meekly inquired, “Do you have any firecrackers here?” The young woman, he recalls, scanned him from head to toe in a slow once-over and then breathily replied, “Just me, honey.” 

Shy and flustered, Stuart admits he left the store that day pretty darn fast, but also confesses that most of his relationships throughout his life have been initiated by women because, as he tells it, he’s a “chicken” when it comes to making the first move. While I rather admire the nervy convenience store clerk, I tend to be a little more like Catherine, a 41-year-old nurse who was taught that nice girls don’tmake the first move. Two years ago, Catherine decided to challenge the rules she grew up with and contacted a guy on Match.com whose profile caught her eye. 

“This was a biggie for me,” Catherine says, “after being raised by a Catholic ex-Marine with four daughters who always said guys will think you are easy if you call them. Of course, he refused to let us pierce our ears or wear makeup because he wasn’t, after all, ‘raising a bunch of harlots.’” Today, she’s still going strong with the man with the intriguing profile. All good-girl Catherine needed to do was take a chance and break out of her ingrained (but outdated) patterns concerning dating stereotypes.


Like Catherine, many women have decided they’re not interested in waiting around and have realized that there are a lot of good reasons why a man might not be making the first move. Here are a few possibilities to consider:

1. He’s not so good at flirting
You might think of it this way: there’s one set of skills that are crucial for initiating relationships (flirting, for example), and there’s a completely separate set of skills for sustaining an established relationship. The man you’re interested in could be very skilled at sustaining a relationship, but have no clue when it comes flirting (and if you think about it, a guy like this might be a very good catch). Remember my friend, Stuart? He belongs to the latter category. “I’ve made the first move a couple of times,” Stuart says, “and they’ve been disasters. One previous girlfriend noted that I have zero flirting skills, which is what most people use to judge the terrain before making a move. Because I just lumber in, it’s usually a disaster. So almost all of my, uh, dates have been initiated by the woman or have been low-risk setups.”

2. He’s just a wee bit intimidated
Remember that annoying “Out of your league” expression? As in, “Don’t even try it, man. She’s waaaaaaaaay out of your league.” Well, as silly as that sort of thinking is to us now that we’re grown, it can linger on in some men’s brains and create confidence-crushing fantasies, such as this one: 1) Glance at beautiful woman; 2) Wonder momentarily if maybe, just maybe, she’d… 3) Have fantasy brutally interrupted by memory of “frenemy” (think Reggie from the Archie comic books or Iago from Othello) jeering: “Forget about it, man. She’s waaaaaay outta your...” and scene. Some fantasy, right?

In fact, I think this is exactly what may have happened to Sara’s future husband, Tom. At the time — some 15 years ago now — Sara and Tom were both working as promoters in the music industry. “People at radio stations all around the country would say to me, in a sing-song voice, ‘Somebody liiiiiiiiiiiiiiiikes you!’” says Sara, now a 44-year-old psychotherapist. “It actually began to annoy me, because I felt that if he liked me so much he should let me know. I refused to make the next move because I thought the whole thing smacked of high school.”

But when Tom did finally work up the nerve to call Sara, her roommate told him she was in Santa Fe for the weekend. Tom then conjured up the idea that if a beautiful woman like Sara were in Santa Fe, she must be there on a romantic weekend with a boyfriend. So, intimidated and discouraged, Tom decided not to ask Sara out. A year later when Sara spotted Tom at a party, she decided to make the first move. “Are you ever going to ask me out?” asked Sara. “I will now,” Tom replied. And he did. They’ve been married for 15 years.

3. He’s been treated badly in past relationships
Maybe you’re a bit like Sara and you’re thinking, “If he likes me so much, surely he can ask me out!” But before you dismiss him on the grounds of “not stepping up to the plate,” stop to consider what he’s been through. A painful, recent rejection — a long relationship ending suddenly against his wishes, perhaps — might be one reason why he’s hesitant to put himself on the line.

Sometimes, making “the first move” doesn’t even mean asking the guy out. It can be as easy as taking the conversation with an acquaintance to the next level by turning it from what’s happening in the news to what’s happening over the weekend. As Sara recalls, “It worked out well, my making the first move, but there was a lot of groundwork to be put down beforehand that helped me make that move a little bit easier.”

Theo Pauline Nestor is a regular contributor to Happen magazine and author of How to Sleep Alone in a King-Size Bed: A Memoir of Starting Over (Crown 2008).