Asking a guy out?

by Madeline Laughs

blissI was talking with one of my single girlfriends the other day and she told me a story about one of her latest adventures in dating. She said she decided not to wait on the guys to ask her out anymore.

Guys do this all the time! They ask girls out. I figured if they can do it, so can I! Well, let me tell you…it’s not as easy as they make it look.

She had been working with this guy for about a year and they had a nice easygoing friendship. She liked him and wondered what it would be like to get to know him a lot better than just as a friend.

So she decided to just ask him out.  

She worked on how she would go about doing this with one of her girlfriends. “What do I say if he says this? How should I ask? Should I just be casual, or should I make it sound more formal?” Once she felt like she was ready to jump in the deep end, she just went for it.

It wasn’t a busy night in the market and John was working behind the meat counter, like he did every night. Teri had been watching him out of the corner of her eye since she clocked in. Finally she had worked up her nerve to walk over and strike up a conversation with him.

She pulled her cell phone out of her pocket to get that one last boost of confidence before heading over. She typed her message on her keypad and hit Send.

Teri: Okay. I’m going to ask him now.

She waited until her phone dinged signalling a response from Susan before taking the plunge into liberated womanhood.

Susan: You go girl! I know he’s going to say yes!

Susan told me that in the numerous conversations she and Teri had about John, her strong impression of him was that he sounded like a total douchebag. “But you know, Teri is my friend and you’re supposed to be on your friend’s side and show support, so I decided not to say anything about how I felt. Who knows? I could be wrong!

Teri walked with purpose right up to the meat counter.

Hi John! How’s your day going?”

John smiled and told her his day was going as expected and asked about her day.

Oh my day is going great so far. You seem to always be working. Do they ever give you a night off?”

Yeah I get Wednesdays off usually” he replied.

This was her opening. She sucked in a deep breath.

I’m off on Wednesday too. Would you like to go have a drink with me this Wednesday night?

John looked up in surprise. Then he quickly turned to face the meat cooler behind him so he could compose himself. After a few seconds he decided he had himself together enough to respond and he turned to face her.

What Teri saw made her want to vomit right there on the spot!

John’s usually happy-go-lucky face was set in a psycho inspired grimace that was supposed to be a smile. His lips were pulled so tightly up and away from his teeth that they looked like they had been surgically removed.

Then he spoke…


His face stayed frozen in the perma-psycho-grin and he stood there looking at her waiting for her to accept his refusal and go away.

Teri was rooted to the spot in shock. In her head she was screaming “Omigod! Omigod! He said NO!” but she forced herself to smile instead. She was trying for a normal smile, but she was sure her face vaguely resembled his face at this awkward moment so she said “Okay” and then bounced away down one of the closest aisles so he wouldn’t see the tears that vehemently burned the backs of her eyelids.

Breathing hard and trying to compose herself, she pulled her cell phone out of her pocket and typed a message to Susan.

Teri: Asked him. He said NO.

Susan: Uh-oh…I’m calling you right now!

Teri: Don’t call. Still really fresh. Will call you later with details.

Teri put the phone back in her pocket just as a co-worker rounded the corner.

Hey. You okay? You look upset about something.”

Teri could just imagine that her eyes were bloodshot and her face was probably beet red too. She shrugged off her co-worker’s concern and told her it was just her allergies and she would be fine. Then she walked across the store to the ladies room so she could have a good cry before going back to work.

How do men do it? How do they keep asking women out on dates? Do they even bother with all of the preparation? Is there even the fear of rejection?

How do they do it without totally losing their minds?

What if a woman rejects their invitation with the same rudeness as John? Does a man head for the ladies room to have a good cry? Or do they just shrug it off and ask the next woman they see for a date, like it was no big deal?

According to an article written by Jen Kim, Valley Girl with a Brain, in Psychology Today:

A question I hear more than any other is whether or not women can ask a guy out. For many of us, the answer is an emphatic: Hell no.”

I’m going to have to agree with that sentiment because for as long as I can remember, women asking men out is taboo. But who is to say those rules can’t be changed?

The article goes on to say:

How do men feel about being asked out?

Well, dating expert Evan Marc Katz, who on his website pegs himself as a “personal trainer for women who want to fall in love,” disagrees with women taking charge in procuring dates.

To the question, “Should women ask men out on dates?” Katz responded no. He warned that women could come across as “aggressive, desperate, and masculine.” Rather, he encourages women to use their “feminine wiles to get men to ask them out.” For example, at a party, women should stand in their potential suitor’s eye line and offer a come hither smile when eye contact is made.

Like Lawrence O’Donnell, does Katz get the last word? Hell no.”

The author of this article doesn’t agree with Katz at all! I don’t blame her. I haven’t given a “come hither” look since I could ride a teeter totter.

At the end of the day, it comes down to your own personal preference.

If you are the type of person who can handle romantic rejection, then you can and should ask out whomever you want. Not to say that you will be absolutely rejected—but, there is a chance that you will hear a “nope”, a “sorry”, or a “not interested.” 

The fear of hearing these vetoes has basically been the burden of men for generations. Lots of guys have learned to brush it off—so it’s not like one rejection will leave permanent emotional scarring.

Or will it? My rejection from a certain Ivy League school still plagues me a decade later. Which is why I don’t like to put myself in those kinds of scenarios. Again, it’s my preference.

Similarly, if you are the type of woman who wants to be traditionally wooed, then don’t ask a guy out. This is the type of person I am. I don’t want a guy to know that I have feelings for him until he makes it obvious that he has feelings for me. It has less to do with being coy than it has to do with being vulnerable. Chet Baker‘s song, “I fall in love too easily” is basically written for me—so it is emotionally safer for me to wait to be asked. Then, I don’t have to worry whether or not it’s a pity date, he doesn’t “like me”, etc.

However, if you don’t care about traditional mating rituals or standard rules of dating (and plenty of people don’t), then you can and should ask out whomever you want. After all, waiting is not all that fun, especially for impatient folks who have places to go and people to see.

 What you shouldn’t let affect your decision-making is what other people deem “right” or “wrong.”

I agree with this line of thinking completely.

“Individuals should be able to make their own decisions, based on what they feel is right for them.

This is your life—you get to make the choices.

If your gut tells you that a guy is interested, but really shy, then follow your intuition. Each potential date is different—so while you may feel comfortable about asking Jim out, you may not feel the same way for Mike.

What does comfortable mean, exactly? Typically, it means you are relatively certain his answer is going to be “yes”.

If you’re the type of person to jump off a roof after you’ve been rejected, then don’t ask anyone out. Why put yourself in a situation that’s likely to hurt you?

Asking a guy out is not so much about the answer that he gives you, but more about how you are going to feel, given that answer. You can and should put your heart and your welfare first.

After all, is there anyone more important than you?

Hell no.”

Should my single girlfriend be asking guys out if it brings her to tears every time the guy says no?


After a few brush-offs under her belt those tearful times will become less and less frequent. Just because she’s a woman, it doesn’t mean she can’t adapt to a man’s way of handling romantic rejection.

Besides, my single girlfriend is adorably cute and a guy should be so lucky to get asked out by her! My friend Susan’s intuition was right…John is a douchebag.

*the names in this story, as it is always, have been changed to protect the innocent…and the douchebags.*

About Madeline Scribes

A writer with a sense of humor. If anyone can laugh at life, it's me.
This entry was posted in All kinds of Advice and tagged , , , . Bookmark the permalink.

9 Responses to Asking a guy out?

  1. Daphne Ogyen says:

    I’m a woman who likes a pretty egalitarian approach (I was also raised in Europe where things are very different in the intragender scripts) caucasian AMERICAN men are the most uncomfortable to ask out. There are many cultural reasons for this… this subject is one of my favorites.

    There are too many attempts at making rules about what really is a case by case kind of set of circumstances. Afterall, you’re not asking the entire male population out, you’re asking one guy you like, at a time. One of the toughest parts is the differences in expectations women and men have in both the mating scripts and the role of sex and emotions in their lives. That being said, men and women both are vulnerable but socially conditioned to expose their vulnerability in different ways.

    Another part is people have bought into this idea of a formula that there is some way someone else or a large group of someone elses know that gets them better scoring. It’s bullshit. no one gets it better. It comes down to how educated and real you are about the cultural matrix you live in. A reason I tend to be attracted to certain kinds of men but not others plays into the social scripts I find familiar. Note I said familiar, not correct. these are primal social wirings in the human brain.

    If you decide to break the “rules” of your cultural process, you had best be prepared to encounter rejection. What’s really tough in the USA is the mishmash of cultures with no exact definition of scripts unless you’re Amish and stay within the confines of your tradtions. In a society that mixes and matches so much, combined with the fact that relationships are largely transactionalized forms of emotional or physical business, these scripts splinter, expectations blur, it’s the biggest most confusing cluster f*** I have ever witnessed in my broad experience of the world.

    When in Rome do like the Romans. But in the US no one really knows the one way because there are so many types amd cultures coexisting with a largely caucasian domination in the media about how-TO’S in the mating rituals.

    I’m European and Asian by blood, but culturally I’m from everywhere. I was fresh off the plane the first time I liked a boy in the USA. I thought nothing of it at 17, I asked him out, got brutally rejected and confused about what I did wrong that made me seem like such a freak to him and his friends. I wrote him a card, told him I liked him and asked him to his face if he’d go out with me and he cowered.

    I didn’t know that as long as I lived in the US I lived on a diet of steady rejection from most caucasian men, so I educated myself. I never had problems with men from anywhere else, so in my world it was truly bizarre how the sexual scripts “changed everything” where in other cultures they are more homogeneous and woven into the intragender interactions to begin with.

    Let’s just say I learned a lot about American men, but it has never stopped me from asking if I liked one. I don’t play games, I’m pretty direct, and don’t feel crushed when rejected. My reasoning is that as a woman of high worth, I’m not throwing my pearls to pigs, if he can’t see it or does not appreciate what I have to offer, it’s no loss.

    This attitude is frightening to most caucasian men. but I get a lot of appreciation for it by African, Latino and European men. plenty more fish in the sea, I realized perhaps the weird scripts many caucasian men hold are not so comfortable for me to start with, so in the US I’ve found myself much less attracted to that group with almost bookmarked rules that are all in their heads and have nothing to do with the reality of the world, love, or even other men. It sure was confusing for a long time though. I don’t know how natives of that cultural madness manage all that neurosis around these invented and largely false rules.

    Who DO they work for anyway?


  2. Maybe that’s a great topic for another post…how to turn someone down gracefully. That night when my girlfriends and I were talking about this incident she also told me that in the future she would be much more considerate in her date refusals based on how this one made her feel.

    I love that you jumped right in there with both feet and asked the guy out and that you two could remain friends afterwards. It’s nice to be able to make those strides in life. You rock at that!


  3. Daphne Ogyen says:

    Thank you for the feedback! I talked about this post with one of my friends, he is also not American. He said something worthy to note. He said there is in his opinion a deep cultural confusion that is directly related to the rapidly changing roles women have in the workforce and technology equalizing the genders.

    For example In a chat, who makes the first move? Men USED TO BE valued for how they provided, women for how they held the house and reared the kids. The roles were pretty straight forward, in other countries women have held working roles longer, so this is in degrees different in more ethnically homogenous countries. Now in the US women work, men stay home, who’s valued for what? All the things that used to be taught just don’t fit the current world, so we have epic confusion.

    Pride still runs high on both sides, but what are we proud about. What do we value in the other genders pride they take in themselves. And then where do we measure shortfalls? The expectations are largely changing and to make it ok we invent rules, fill the void with stats, trends, all to make ourselves feel like we know what’s up. But no one really knows better than anyone else. The key is to just listen and go with it the most human way we can.

    How to turn down that guy who thinks they can be our one? Be kind, but don’t mess with him. Be uncomfortably direct to leave no room for guessing, but be kind. The reason I say be uncomfortably direct is because most of the male population has been taught that women are weak thinkers and that no means maybe or even yes. Ugh. That with a little convincing, you’ll go for it. A little discomfort in being clear goes a long way to even shape a friendship out of a setting a guy straight if he is worth that investment. Communicate your expectation to him and how it differs from what you hear he is asking. If you’re wrong, great. He really thought you’re great but wouldn’t sleep with you. If you’re right about his intentions in how you heard his interest asking you out, great. You be clear and everyone is clear.

    The point is you are your guardian, your own advocate, and most of all the owner of all your interpersonal dealings. Treat saying no the way you would want to be told so you don’t chase somehing that doesn’t exist anywhere but in your head. Own being upfront, be the woman the man you seek would be proud to have as his companion. everything else will take care of itself. #whatrules?


  4. Great post. This made me feel so much better about my inability to make the first move if i am interested in a guy…..just cant do it. Now I feel okay about that, seeing that I avoided the horror suffered by your friend above.


  5. Pingback: Let him down Easy | Spread Information

  6. I couldn’t disagree more with all the so-called “professional advice” quoted in this article, and I agree with this blog author.

    As a single American male in the US, I would be *flattered* if a woman asked me out. I have an outgoing personality, but it’s largely a ruse. When it comes to the “seriousness” of asking a girl out, I HAVE NO IDEA WHAT TO SAY OR HOW TO ASK. I’ve done it maybe two or three times in my life, and it’s usually after several *months* of casual flirting and immediately preceded by a near panic attack. My heart rate increases, my face gets warm, and I know my speech is fast and clipped. In the rare case of acceptance, I all-but jump in the air and clap my heels in excited victory. After rejection, my response is to try to act like it was no big deal and walk away, but I can tell I’m walking briskly and avoiding eye contact with everyone because I just want to GET OUT. I imagine this is similar to the reaction your friend had. This is *not* gender specific.

    Just because a guy has traditionally been responsible for doing the asking does *NOT* mean it’s “easy” for us. In fact, I would argue that the only ones it’s “easy” for are the ones who are just looking to score and if you say no it’s not a big deal because they’re not hurting for “easy dates”. There have been several women throughout my life that I wanted to ask out, but by the time I worked up the courage, they informed me they had a boyfriend (and I knew they didn’t previously). For some men, just like women, working up the courage is hard.

    Ladies, please – if you’re interested, DO NOT BE AFRAID TO MAKE THE MOVE. This goes for more than just the first date, too. If you’re hoping for a kiss, DO IT. If you want a second date – even if the guy asked for the first one – DO IT.

    A person who is worth your time will say yes. A person who says no is not worth your time (with the possible exception of they’re already in a relationship – they may be worth your time, but just unavailable). These facts are true regardless of whether your genitalia is an “innie” or an “outie”.



    • Daphne Ogyen says:

      rejection is hard for anyone with a beating human heart. life is short. if you want him or her, follow Nike’s sound advice. just do it. she is the Greek god of wisdom and awesome sneakers for a reason..


  7. Pingback: Let him down Easy | Madeline Scribes

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