Joshua Snodin, 06.01.2015

Should I ask him out? How to be daring when dating!

According to a recent EliteSingles survey, just 6% of women would suggest a first date and just 2% would call back to arrange a second.(1) While this appears normal, the surprising responses from men in our poll may hint at a problem with this dating routine.

As many as 25% of men said that they expect to be asked out. With female participants in the survey also expressing considerably less excitement before a date than men, this suggests that women could have more dates, and probably better ones, if they took the initiative more when dating. EliteSingles asked dating expert Marni Battista for her thoughts on what women can do to redress this imbalance if they're thinking "should i ask him out?"

graphic showing who should ask someone out

Should I ask him out? Dating with courage

Throughout dating literature and countless conversations amongst single women, it seems to be the general rule of thumb that men should be the initiators of every step of the dating process - from the first conversation, to the first date, to the first kiss and so on. While it’s true that the dynamics between each coupling are different and should be treated as such, I fear that many eligible women are missing out by going radio silent.

In order to help you unpack some of the preconceived notions and deep-seated fears that led you to your wallflower status, here are some common misconceptions that women face when wondering ''should I ask him out?'' Just remember, that's all they are: misconceptions. With a little thought adjustment you can learn how to overcome them and become a more proactive dater -  in a way that also embraces your feminine energy.

1. Initiating is seen as aggressive and desperate. (And too masculine!)

Whether it’s something our mums advised us growing up or the fact that women in movies who ask out guys are always depicted as outgoing, overbearing and aggressive, we women have turned into shrinking violets for fear of coming across as too masculine. Not only that, but we feel as if the act of blatantly asking out a man will cause us to appear desperate and send the wrong message.

However, there are ways to take action without foregoing your feminine energy. Rather than charging up to a cute man at a bar and asking him out up front, use your feminine wiles to get the ball rolling. If you see someone cute you’d like to talk to, place yourself in his line of vision and smile at him when you make eye contact. (Obviously smile, ladies; a quick .012 second half-smirk will not cut it!) 

If you’ve been talking to a man in a friendly context but are interested in taking it further and sensed he may feel the same way, get a little flirtatious and see how he responds. Maybe even suggest a new “must” in your city as something on your bucket list and see if he takes the bait by suggesting you both go there together. Taking action doesn’t necessarily need to be done in an “aggressive” manner.

READ MORE: Need help mastering those flirting skills? Learn how to flirt here.

2. Initiating leads to a loss of power.

The fear that simply initiating interest will immediately give the man the upper hand in the relationship and put your delicate feelings in his hands is a strong and often valid one. There are lots of men out there who get some kind of power trip off having control in a relationship and abusing that power, and perhaps some of you developed this fear because of a particularly scarring experience

But much like any other part of life – be it work, a favourite activity of yours, or moving to a new city – the greatest rewards often come with some initial risk. Before taking the leap, mentally prepare yourself for the possibility of rejection. Just remember that the worst result is for him not to return those feelings. If he chooses to express his disinterest in an insensitive manner, then he’s not someone you want to be with anyway. Simple as that. So, see #1 above and take a risk. Smile longer than what makes you comfortable. Strike up a conversation with the cutie at the bar, and ask him to hold your drink while you “dig” in your purse for something.

READ MORE: Want to know how to be courageous online? Try our dating advice for women!

3. Initiating makes you vulnerable.

On a similar note, many single women use their inactivity as a shield that can easily be misinterpreted as disinterest. Defence mechanisms run rampant in the dating world, and rare is the occasion they help move one’s love life in a positive direction. If you’ve felt that your love life has been pretty quiet the past few months, can you think of at least five instances in the past five months where you could have struck up a conversation with a guy but didn’t? Or suggested meeting up with a man you’ve been texting with in a friendly context for weeks on end? My guess is that you can, but are just now realising that those were opportunities after being blinded by that ever-present defence mechanism.

Luckily, the first step to solving this problem is recognizing that you have it. Reflect on those missed opportunities and imagine what would have ensued had you commented on the horrible in-flight movie to the cute guy next to you on the plane. Unless he has a very specific kind of social anxiety, odds are he would’ve responded...and within a few minutes, you would have a sense of whether he was attached or interested. Or what if you had mentioned to the endless-texter a cool new hiking spot you’ve discovered? The worst he could have said is no (Are you sensing a theme here?), and there’s your answer: a simple no. In either case, both could be passed off as you simply being friendly and trying to make a connection with someone, no defence mechanism included.

READ MORE: Learn how to overcome dating anxiety and become emotionally ready for romance

4. Initiating means he never liked you in the first place.

I’ve heard way too many single women use the “if he were into me he would’ve asked me out already” excuse when explaining why they haven’t gone after a man of interest. We apply a gender-focused double standard to equal salaries and power in the workplace, so what makes it different when it comes to dating? I’ve written many articles on reading the signs of whether or not a man is into you as more than a friend, and that advice is especially applicable when determining whether or not to take the dating initiative with a certain man. 

Is he singling you out? Asking you specific questions about your life? Remembering your answers later and referencing them in subsequent conversations? There are many signs you can look for that can easily point to a man who’s just as interested and also just as fearful of making the first move. If you feel confident that he’s interested or are willing to take that risk, by all means let him know you’re interested. Or at the very least, let on your interest to a mutual friend who can discreetly pass along the word. And if you feel strongly enough after reading this article, just go ahead and mention you would enjoy an opportunity to hang out again one on one. 

READ MORE: Take the fear out of initiating by learning how to write the perfect first message

Just remember that as you’re evaluating your initiating track record and determining how and when to move forward with your new mission, men are just as prone to being shy and insecure as girls, and sometimes all they need is a push in the right direction. You’ll know a confident, Alpha Male when you see one, and those are perfectly capable of initiating without much nudging from you. But if you’ve proactively made it clear that you’d be open to a romantic relationship and he’s still not meeting you in the middle, it’s time to find someone with whom you can strike the right balance!

Still wondering 'should i ask him out?' The answer is clear: yes! Find someone wonderful to strike a balance with - join EliteSingles today.

If you have any questions, please leave a comment below or write to us at

EliteSingles editorial, December 2013

This article was written by Marni Battista, a dating expert and life coach at Dating with Dignity.

Total votes: 382
Did you like this article?
Review for "Should I ask him out? How to be daring when dating". Average: 3.32 out of 5 based on 382 votes
More comments