How Do You Get a Passive Guy to Ask You Out?

This guy is driving me nuts. He seems to be interested, yet he’s not doing anything. What the hell is up with him??”

I shrugged and stared at my beer. “Maybe he’s just a passive guy. They need a little more time to warm up.”

She shook her head. “Well, I can’t wait forever.”

I took a gulp of beer, cleared my throat, and sat up. “How much do you like this guy?”

“I like him,” she whispered into her beer. “A lot.”

“Would you be willing to put in a little more effort to see if it can go somewhere?”

She sighed. “I feel like I have been and it’s going nowhere.”

“Okay, here’s what you can do.” My voice and volume increased. I pushed aside my beer. “Flirt with him. Give him little signs to know you’re interested. Give him some openings and chances to ask you out.”

“Mike,” she said right into my eyes. “I’ve read your site. I know all about your tips on flirting.”

“Oh,” I said.

“I’ve done them all.”


“Every single goddamn one.”


She sighed again. “I’ve dropped hints like crazy. I told him I wanted to see I Am Legend. And he actually took me to see it! But then, a week later: No phone calls, nothing. Then I called him and he seemed happy to hear from me. We actually talked for hours.”

“Oh, how was it?”

“They were good. We talked about everything—”

“No, I mean the movie? How was I Am Legend?”

“Oh. Eh,” she shrugged. “It was okay. Don’t expect too much.”

“Too bad. Sorry, I didn’t mean to interrupt. Go on.”

She cast a glance at her beer. “Well, that’s about it. We talked for hours, then nothing. Sometimes it feels like there’s chemistry, sometimes there doesn’t.”

We both went back to our beers, nursing them gently. I savored the suds and sweet, bitter taste. It was a delicate flavor, tippy-toeing on my tongue without stepping down firmly.

“Tell me about him,” I said. “What kind of guy is he?”

“Well, he’s kind of a quiet guy in groups. With me alone, he’ll talk for hours though. When he’s in groups, he’ll sit back and be more of a listener. He’s definitely passive. I think every time we’ve gone out, it’s mostly been because I nudged. And we’ve only gone out like twice so far, the movie and a lunch before that. Every other time, it’s been in group settings.”

“And what do you like about him?”

She rattled off a list of traits like she was naming favorite albums. Her eyes widened, almost swooning a little. There was a hint of a smile on her lips too. She definitely liked him.

“And you’ve flirted with him? Given him signs?”

“Everything. All of it. Making eye contact. Laughing at his goofy jokes. Sitting up close to him. Everything except straight up asking him out.”

“Would you ever?”

“What? Ask him out?”


She wrinkled her brow. “I don’t want to ask a guy out. A guy should ask a girl out.”

I stretched my arms. “Ahhh yes, that age-old debate. Who should ask out whom.”

“A guy should ask a girl out.”

“I see chivalry is not dead in the new millennium,” I chided.

“It’s not just about chivalry. Guys like to chase girls, right?”

“Well, I don’t know about that for all guys…”

“Most guys do. And if a girl asks a guy out, there’s no chase. That means there’s no challenge and he’ll eventually lose interest.”

I laughed. “So if a guy gets to chase a girl, he’ll automatically fall in love with her? Just because of the chase?”

“No, no. I’m saying that guys like the chase. It adds to the excitement of dating. But if a girl gives in too easily, she’ll seem desperate or worse, a floozy.”

“A floozy?”

“A floozy.”

“I like that word. I’m going to use it from now on.”

She scowled. “You’re making fun.”

“I’m totally making fun. Not all guys like the chase. If a girl plays hard-to-get, that may work on some guys, but not all guys. And I guarantee you that this guy, since he’s so passive, would NOT react kindly if you played hard-to-get.”

She sighed and resigned into her chair. “You’re probably right. He’s done squat already. I’m already playing easy-to-get, and he’s still not getting me!”

I laughed. “At least you’re not a floozy!”

She gave me another scowl.

“Okay, here’s one theory. It’s a controversial one, but I’ve heard it from a lot of people, both guys and girls.” I cleared my throat and sat up straight again. “Some believe that one of the side effects of feminism and the growing empowerment of women is the demasculinization of men.”

She started to squirm in her seat. Her eyes lowered on me with an intense gaze. I paused for a moment. “Okay, okay, let me try to qualify what I’m saying. I don’t mean to offend at all. I’m just relating what a lot of guys, and some girls, believe. In the context of this theory, feminine and masculine refer to the stereotypical gender roles of Western society. So the demasculinization of men means a change in the traditional gender roles of men.”

She tilted her head back slightly. It was sort of a nod, but not really. I continued. “Some men supported this equalization of gender roles so much that they no longer behaved according to the traditional rules. In some cases, this is good, as seen in the workplace and in the family. You now see many more men doing housework, raising children, etc. But in other cases, this perhaps isn’t so good. Like in the case of who asks out whom on a date.”

She opened her mouth, but I continued talking. “Know the old rule that a guy should open a door for a woman? I’ve met some women who get offended when a guy does that. It’s rare, but they’re out there. And many guys don’t want to offend or come off insensitive to women’s rights. So what happens? They switch roles. They stop opening up doors for women, they let women ask them out, etc etc.”

Her eyes were blazing now. “Are you done?”

I gulped. “Um, yea.”

“Okay, first of all, I get what you’re saying. The twenty-first century guy wants to be sensitive to gender equalization. But that’s not the same as a passive guy.”

“Maybe not, but they’re related in this particular case. There are passive guys and passive girls; passivity is not gender specific. When you pair up a passive person and an assertive person, it’s generally the assertive person who dominates, right? So look at you and this guy. Who’s the assertive one? Clearly, you are. Therefore, it’s up to you to make the first move.”


I shook my head. “There are no buts. The whole gender equalization discussion basically says that you should strip out traditional gender roles from your situation. He’s no longer the guy and you’re no longer the girl.”

“Great, thanks.”

“Sure, anytime. So without gender roles, what we’re left with is a passive person and an assertive person. And that means the assertive person is the one who has to make the first move.”

She sighed and slowly let her head drop. Her hand lazily grabbed her beer and drew it towards her. “I guess you’re right. But…” She looked out the window. I followed her gaze and we silently watched a couple holding hands walk by the bar.

“But,” she continued, “I don’t want to have to ask a guy out. I like it when a guy asks me out. It shows… I don’t know… It shows that he’s a man.”

“So much for equalization of gender roles,” I muttered.

“Maybe I’m just an old-fashioned girl, I don’t know.” She watched the couple until they disappeared from view.

“Personally, I think we just happen to be living in a time where all kinds of traditional stereotypes are being questioned. Whenever convention wisdom is confronted, there’s always an awkward period of confusion. It’s like puberty for social evolution. Before we can settle down on whatever it is we should, we’re going to have to deal with deepening voices, hair in funny places, and wet dreams.”

“Great analogy Mike, thanks,” she smirked with an eye roll.

“As for you, I think you’re going to have to ask yourself: ‘Do I like this guy enough to get past his passiveness, risk rejection, and ask him out? Or is he not worth it, because he’s not being a man and asking me out?'”

She shrugged and kept her eyes out the window. “This is why dating sucks.” She took a monstrous gulp of beer, finishing off her glass until only suds remained. Then she ordered a new beer. “Maybe I will ask him out.”

I scowled at her. “Ew, you floozy.”

Author: Mike Lee

An idealistic realist, humanistic technologist & constant student.

13 thoughts on “How Do You Get a Passive Guy to Ask You Out?”

  1. Tell yer friend to just ask him out. At least, she’ll stop tormenting herself w/ these questions =) Some guys are passive, most are clueless (including m’self).

    Well that’s worth a pair of pennies.

  2. It all comes down to what she wants. If she wants a guy who’ll ask her out, this is cleary not the guy for her. If she wants this guy, she’s gonna have to buckle down. Since subtlety doesn’t work with passive guys, she’ll need to say something like, “are you going to ask me out or what?” But seriously, I’m not sure any girl would really be happy with a guy who doesn’t have enough guts to ask her out. If he can’t step up and do it, he doesn’t deserve to have her.

  3. The typical girly-girl would employ a friend as The Spy.

    Get The Spy to buddy up with the Guy and have Spy pretend to “tell a secret” to Guy that Girl likes Guy.

    Spy doesn’t even have to come out and say it directly. Spy could say something like, “You know, Girl talks about you constantly.” Spy should make some sort of commentary that will incite Guy to inquire further. “Oh yeah? What does she say?” Something that piques his interest in what Girl thinks of him.

    Spy should then beat around the bush with how Girl thinks oh so positively of Guy. Have Spy bloat up Guy’s ego through what are purportedly Girl’s thoughts.

    Once Guy gets that glassy look over eyes, Spy should give him The Nudge and say, “You know, if you’re really interested, you should ask her out, let her know. And if you don’t do it soon, you’ll miss your window of opportunity, she’ll move on, and you will lose out on what could have been really phenomenal chemistry.”

    If Guy still does not respond in the affirmative, then Girl should just move on. If a guy doesn’t even have the backbone to assert himself in such a situation, he’ll never have the backbone to assert himself for the greater good in life.

  4. I don’t want to ask the guy out. I have been the one to ask almost every time bc I have no patience, but if I have to, I will again.The only thing is that I have to be certain that he will say yes, after many tests.
    However at the date, he has to make some moves. One person shouldn’t have to do ALL the work. And you have to know if he accepted bc he likes you or just didn’t want to hurt your feelings. But you should know that already by the way he accepts. If its a struggle, then retract by saying that it’s ok, you will fond another to do wtv it was that u wanted to do. Don’t communicate for at least a week and don’t ever bring up the subject again, if you want to remain friends. It will save your pride and confidence.

  5. Heh .. passive guy. Yep. Well, I’ve had to go by how he responds when I suggest stuff to do together. Most of the time he’s all for it, and occasionally he’ll even invite me somewhere, like on a couple of his contract jobs. Then he took me out for pizza.
    He’s not a lost cause at all, but it forced me to dispense with the stereotype and to really observe how he behaves over time toward me.
    We ‘get’ each other’s sense of humour, it’s so easy to be with him, and he grins with this dopey-eyed giggle that melts me every time.

    Don’t underestimate how nice it can be to feel free to call him if you want to. This kind of man doesn’t mind.

  6. Love the story. Very insightful and I do agree that feminism came with some unexpected cons! I hope to meet a super guy who can be traditional and contemporary b/c that is exactly the kind of girl I am.

    love & hugs to all

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