How to Ask a Guy Out on a Date In 10 Easy Steps

How to Ask a Guy Out on a Date In 10 Easy Steps


The dating world can be one of great elation. There’s the excitement of the first date, the first kiss, and infatuation that can often lead to the beginnings of a passionate, fulfilling relationship. Conversely, dating can also be a source of stress and anxiety — enough to lead us to deeming ourselves forever destined to the single life, throwing our hands up in the air as we exclaim, “I quit!”


For women in particular, we often find ourselves in today’s current dating culture unsure of whether or not to initiate romantic gestures, and — even when we are sure of our interest’s likelihood to reciprocate — we are often afraid to eschew convention and be the one asking the man out for a date as opposed to waiting to be asked. Shouldn’t we be the ones who are getting pursued? Isn’t it the man’s job to do the asking?


No, it’s not. Perhaps decades ago when various gender stereotypes reigned supreme, and gender roles were extremely concrete, this was true. Much has changed during the late 20th and early 21st centuries, and with these changes comes a newfound independence for women. Not only are we able to take greater control over our professional lives, we also have more freedom within our romantic lives. Still, asking a man out on a date continues to be something that is approached gingerly by many women.

I’m here to present to you ways that you can turn those ginger steps toward a man you want to ask out on a date into giant strides! Let’s take a look at how to ask a man out on a date.

10Make Eye Contact & Rely On Nonverbal Cues

Make a little eye contact.

For decades (centuries?), men have taken on the brunt of the initial “courting” period as far as the dating scene goes. What many of us being newbies to asking men out , we often don’t realize this simple fact: it’s just as nerve-wracking for a man to approach you as it is for you to approach him. The fear of rejection can be a very pervasive thing; not only that, it is often a culprit in hindering what could be the start of a worthwhile relationship. Approaching with a warm smile and confidence can help you not only signal to the man in question that you’re interested — it can help you lock down a date almost instantly!


According to the Social Issues Research Centre’s (SIRC) Guide to Flirting by Kate Fox, many nonverbal signals can help preface things like flirting, asking someone out, and even a first kiss! “Even from across a crowded room at a party, you can signal your interest in someone merely by making eye contact and attempting to hold your target’s gaze for more than one second (not too much more, though, or you will seem threatening).” Fox goes on to note that reciprocation of these verbal cues — such as the man smiling back, holding your gaze for more than a few seconds, and mimicking your physical position and gestures — can be a green light that he is just as interested as you are.

9Send or Buy Him A Drink

Buy him a drink

Have you caught a prospective suitor’s gaze from across the bar? Are you out with friends at a favored watering hole and you have found yourself alone with a crush? “Sending over a drink” has been a staple way for men to approach women they fancy for years, so why not practice this successful move yourself? There are a couple of things to keep in mind before trying this move, however, such as:


  • What is said man’s poison (alcoholic beverage) of choice?
  • How can you figure out what drink he will enjoy?
  • What do you do afterwards?


If you are not running with the same group of friends as the man you want to ask out for a date, eye up what he orders from the bar or what he already has on hand, and order him another round. Not only will his thirst be quenched, you’ll be offering a stealth signal that you’re interested. Once the drink arrives, you can offer up a flirtatious anecdote, such as: “It looked like you’re glass needed some refreshing,” and start a conversation. From there, you can work your way up to asking for the two of you to have a drink together again in another location when both of you are available.

8Gauge If The Man Is Who You Really Want To Be Asking Out

Does he have a secret?

If you are the type of woman that finds herself willing to eschew archaic views on courtship and defy convention by being the one to take control and do the asking — congratulations! You fit well into the fabric of the 21st century, one that has been marked with great progress for women and has dismissed past conventions that were perpetuated for decades in the dating world. Still, not everyone is going to have the same progressive mindset as you. Does the man you are interested in dating hold the same views? If you have found yourself so attracted, it is likely that he does. Although “opposites attract” has made its way into cliched vernacular, it is much more common for romantic couplings to include like-minded people.


If you haven’t already, try to learn a little bit more about the potential apple of your eye. Are your views compatible? Do you laugh at the same things? Do you take interests in similar activities? If the answers to these questions renders a resounding “YES!” then this man is someone you should seriously consider asking out on a date.

7Wear Something You Feel Comfortable & Confident In

Wear that perfect LBD

You look great in whatever you wear — trust me on this one! However, there is nothing wrong with taking time to pick out an ensemble that makes you feel absolutely grand in anticipation of taking the plunge, and asking a man out. Take some time to yourself to try on different outfits until you land on one that makes you feel absolutely fierce. Although appearances aren’t the most important aspect of attraction (far from it!) feeling confident in the way you look doesn’t hurt in taking on what can often be a nerve-wracking experience. Not only does a pleasing outfit make you feel confident, you will unwittingly be exuding this confidence, which can help you find the proper words in asking a man out and also make you more attractive and appealing.


Notice that I made confidence the most prominent facet of attractiveness here as opposed to the outfit. Like women, men are attracted to confidence and some who seems self-assured enough to take initiative. Basically, if you  believe something to be true, others will as well. This belief is taken from the old adage of a “self-fulfilling prophecy,” a term first coined by Robert Merton in 1948. As aged as the term is, it still rings true today. I can say personally that there are a litany of instances of success I have accumulated simply by believing that said instance was true, and thus my belief made it so. Conversely, when we hold onto the belief that we are doomed for failure, this belief can also come to fruition, no matter how fallacious its roots are.


Help your positive beliefs along by pampering yourself with an outfit you look amazing in (check you out, girl!) and even pepper in a pedicure/manicure or a blowout if you feel so inclined. Even if the man in question’s answer is “no” (how dare he?!), you’ll be confident enough to find a new potential suitor pronto.

6Break The Touch Barrier

Reach out and touch someone

OK, it’s true story time. I was once on a date with a man without even realizing it was a date. My suitor and I were seated at a bar, enjoying casual conversation and some cocktails, and I noticed — much to my delight — that the conversation took a very flirtatious turn. As things began foraying toward the romantic, my date made his interest known in a very stealthy way known as “breaking the touch barrier.” Breaking the touch barrier involves casually — yet noticeably — touching the person you are conversing with on an innocuous region such as the shoulder, upper arm, or elbow. It may seem simplistic, but trust me, it works.


According to Art of Charm: “Touching bridges a gap between you and the [person] you’re talking to. The physical connection helps the emotional connection between you deepen. Not only will [the person] feel more comfortable touching you, [they will] feel more comfortable talking to you.”


I know that for me, an innocuous touch has helped ease the conversation into more intimate territory, which also helped me build the confidence to coquettishly suggest, “You and I should do this again sometime,” or “What is your schedule this week? I’d love to get together with you when we’re both free.”

5Do Some Investigation

Get snooping

This point builds a bit on number eight of our list. What would happen if you finally mustered the courage to ask a man out on and date and found out that (gasp!) he is already attached to a serious girlfriend or is married. Not all men wear wedding rings, and sometimes this isn’t for a lascivious reason — they simply don’t prefer wearing jewelry, or may have even grown out of the ring. Hey, it happens. You don’t want to be in the awkward position of asking a man out only to learn that he is attached or — even worse — have his significant other intervene during your attempted flirtation.

To avoid this, try to assess whether the man in question is attached beforehand. If you have mutual friends, you can easily gain access to this information from someone trusted by casually asking if they are seeing anyone. If you don’t have access to any mutual friends, you can work this point into the conversation without making your attraction obvious. For example, if you both meet by happenstance in a cafe or favored watering hole, you can insert something into the conversation, like: “My [choose whether you want to say “friends” or “ex-boyfriend,” both which signal that you are currently unattached] actually introduced me to this place a while back. Have you brought your girlfriend here? A lot of people say this makes for one of their favorite dating spots.” A smile and a “no, I don’t have a girlfriend,” is the perfect way for you to continue the conversation (don’t forget to return his flirtatious grin!) and work your way up to suggesting the two of you reconvene for an actual date.

4Have A Spare Ticket

Guys love tickets. Especially free tickets

Whether it’s a concert, local event, wine tasting or what have you, we’re all going to be purchasing tickets at some point. Find an event that you genuinely would be interested in going to — regardless of whether or not the person you would be taking would be of a romantic persuasion — and purchase two tickets. If possible, make sure it is also an event that you know the man would be interested in attending, and one he doesn’t already have tickets to.

You don’t have to lie and say somebody cancelled on you when bringing up the fact that you have a spare ticket. As the conversation moves toward interests, simply bring up the fact that [insert event of your choice here] is happening on such-and-such a date and you happen to have an extra ticket. Would he like to go? Of course he would! Even if he is unavailable on the date that you suggested, you can move the conversation toward dating at this point, since you have already made him aware of the fact that you would be up for seeing him again one-on-one. Regardless of the outcome, you’ve at least offered yourself an event that you’re going to enjoy, and can invite a friend instead to said event.

3Suggest A Group Outing

Get the gang back together

Heather Jensen of allwomenstalk offers an excellent anecdote on the benefit of asking a man out on a group date as opposed to something more intimate. She states: “I  admit, it’s really hard to learn how to ask a #guy out, but if you invite him on a group date, what’s the harm? Make it a mixture of his friends and yours. That way, nobody is left out and it won’t be awkward. Who knows, maybe it’ll be a great #time for you to meet his friends!”

A group date can save you some anxiety, because group dates by nature are casual, and don’t even necessarily have to constitute as a romantic “first date.” If he says yes, this offers you a further opportunity to allow your personality to shine, without the pressures that many intimate first dates bring. Throughout the night, you can continue your flirtation and suggest a time that both of you could get together one-on-one based on your mutual interests and preferred location.

2Be Prepared For Rejection & Don’t Fear It

“I wish I had two more hands so I could give you four thumbs down.” Get used to rejection

I know being unafraid of the potential of rejection is much easier said than done. One of my favorite quotes regarding love is by the late and great Peter Williams. He said: “It is a risk to love. What if it doesn’t work out? Ah, but what if it does?” Although you’re likely not “in love” with someone you are only thinking about asking on a first date (or maybe you are), this quote reminds us to take risks, even if those risks are peppered with crippling fears of things like rejection. An article from Uncommon Help outlines the roots of fearing rejection, and the dismantling effect said fear can have on our everyday lives and interactions.


“If we feel that rejection will mean the ‘end of the world’ for us, then we will fear it all the more. It (the fear) has power over us,” writes Uncommon Help’s Mark Tyrrell. “But if you sit down and think: ‘Okay, if this relationship does end, how will I manage?’, you are facing your fear constructively. Of course you’ll survive and you may even thrive. Knowing you’ll be okay whatever happens gives you huge amounts of confidence and makes it easier to finally switch off the old automatic rejection detector (which is faulty anyway).”


Moreover, if someone you are interested in dating rejects your invitation, consider this: perhaps that person wasn’t the type of man you really wanted to be on a date with, after all. This is not to say that the person you wanted to go on a date with is a “bad person” — far from it! All this means is that the two of you likely may not have meshed in a way that you assumed. I have been through rejection, I have been the one rejecting, and I have also been broken up with as well as the initiator of breakups. Throughout my many experiences, I have come to understand that none of these instances had to do with me or the other person being better or worse than the other, or being more or less attractive and desirable. Romantic relationships differ from friendships in the way that it takes a myriad of intricate elements to make two people attracted to each other, for two people to have winning chemistry, and for two people to mesh in a way that a romantic relationship can be successful.


When being rejected, it is easy to fall into the pervasive trap of self-criticism: “What did I do wrong?” “What is wrong with me?” Nothing is wrong with me, and there is nothing wrong with the other person either. The person that does the rejecting often just — for whatever reason — was quicker in recognizing a conclusion you would have also come to eventually: the two of you are simply not right for each other in a romantic sense.


Be prepared for rejection, and — if it happens — treat the rejection (as well as yourself) with a smile and a candid “OK.” It’s not the end of the world, trust me.

1Just DO IT, Already!

If you don’t ask him out some other bimbo will

When it comes to exactly how to ask out a man you are attracted to for a date, one thing that you cannot avoid, and cannot be further expounded on in a “do’s” or “don’ts” essay, is the fact that you are ultimately going to have to swallow your fears and just do it, already! We’ve already talked about facing rejection, ways to insinuate your desire for a date, and methods to prepare. Now the time has come for you to make a serious move, and potentially score an awesome date for the current source of your amore. Do you need an extra confidence boost? No problem!


BuzzFeed took to the question of whether or not women should ask me out by surveying both women and men. The overwhelming conclusion by both women and men was a resounding “yes,” women should ask men out, and that this assertiveness can actually be a huge “turn on” for men.


One woman stated that — although she initially was reticent to ask a man out for a date — she found the experience “so empowering” and concluded: “if you want your man, go get your man!”


To turn the tables, men also provided their two cents on women who ask them out for a date. Due to past conventions, a few mentioned that women approaching them for a date made them wonder if they “had waited to long” to take initiative when a woman asked them out for a date, as that wasn’t something they were previously used to. Still, the overwhelming majority of men said they found a woman asking them out to be “a major turn on” and one even posited that such a gesture would make him “…be 10 times more likely to buy her a nice dinner.” Another made a call to action on changing dating conventions, saying, “Let’s just get over this pretense of who’s supposed to pursue who, and just go after the person we’re attracted to.”


Now that sounds like something I can get on board with.