Our New Wise Guys Advise Women on How to Ask Men Out (Part 1 of 2)

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A few new men have joined the ranks of our Wise Guys! They’ve all answered the following question: “What’s the best way for a woman to ask a guy out?” Meet half of them below, then tune in next Tuesday to meet the rest!

Married Bisexual Guy (Bryan Sebeck): It’s not as simple as it sounds, but be direct, confident, and unambiguous. First, guys are pretty terrible at reading subtext. Unless you’re pretty blunt with us, we won’t notice that you’re actually asking us out because we’re too busy trying to figure out the best way to ask you out. You don’t need to hit us over the head with the obvious stick to get your point across, but you’ll need to be a little more direct than you think you ought to be.  Second: guys love confident women. The problem is that there is a fine line between confident and intimidating. The intimidating thing works with some guys (I have a thing for women who can beat me up), but stick with just confident unless you know him very well. Smile, make eye contact, and be honest. If you’re a bit nervous, it’s ok. Welcome to the club, ladies. This is how men feel every time we even consider talking to a woman. Lastly, be unambiguous. Most guys aren’t big fans of the words “some time.” If you suggest a specific date, or even time period, you’ll be ahead of the pack. Try “I’d like to go to dinner with you next week.” Dinner is a horrible date, but that’s a whole different question to answer.

Single Straight Guy (Megan): I met Beth for the first time in a friend’s dorm room while in college. A few of us were waiting for her so we could all drive down to a party in Austin, Texas. She showed up wearing blue jeans, a green t-shirt, and plaid Doc Martens. She had pale skin, a light dusting of freckles and dark, red hair. She was an English major and a smart-ass. I liked her immediately. Plus, she brought some dope. That meant everybody in the dorm room liked her, too. Once we were in the car and en route, we all started talking about upcoming movies we wanted to see: “Immortal Beloved,” “Pulp Fiction,” and “Quiz Show” were the popular ones on that ride. Beth started talking about “Crooklyn.” I told her what I thought about Spike Lee. Boom. There it was. Just like that. She turned around in the passenger seat to face me and two other people in the backseat and said, “Hey, wanna go on a date?” Straight-up, honest, direct and confident. That’s how you do it. No games. No fuss. No potential for misinterpretation. No fear. Men need women to be direct. Always. You want me to take out the trash? Just ask me. You want me to buy groceries? Just ask me. You want me to go on a date with you? Don’t give me signs. Just ask me. (Bonus points if it’s in front of friends. Serious bonus points.)

Committed Gay Guy (Dwayne): Well, in my limited experience, when you first meet a guy you have sex and then decide if you want to go on a date with him. I’m pretty sure that doesn’t happen often in the world of straight dating. I’m a bit of a old-school traditionalist, so I would say that a woman should give her phone number to a potential date, to show interest, and then let him call her to make plans.

Single Straight Guy (Saad): Two things to do when asking a guy out: 1) Be direct and 2) Get out of the way. What you want is one-on-one time with him. Be direct when you ask for it, e.g., “Let’s have a beer together.” If you’ve already experienced some sparks, that’s all you have to say. If you haven’t had much previous contact, you might want to justify lightly — something like “I thought your poem/article/iPhone app was cool!” Once you’re together, you can gently indicate your romantic interest, but I say “get out of the way” because men are wired to make the first move. If his interest in you grows, and he has got a clue, he will recognize your interest and act on the mutual attraction.

Our “wise guys” are a rotating group of contributors, some of whom wish to remain anonymous and some of whom like the attention. This week’s Married Bisexual Guy is Bryan Sebeck, a newlywed engineer and artist working in Detroit, MI who blogs at A Yooper Steampunk; our Committed Gay Guy is Dwayne Resnick, a mid-20th-century decorative arts dealer in NY’s Hudson Valley; and our Single Straight Guys are The Meeglet blogger Megan, a former librarian whose Men of the Stacks calendar benefits the It Gets Better Project, and Saad Hasan, who works on nanotechnology with a team in Pennsylvania. To ask the guys your own question, click here.


  1. Actually, one of the handsomest young men I ever met (who was also quite nice) had some trouble getting girlfriends because everyone tended to assume he was either gay, taken, arrogant about his looks, or all of the above. Not that it’s the worst problem one could have — just saying he didn’t have it especially easy.

  2. Amen,Dallas! You said it! Women like REAL men. The pretty ones are usually too stuck on themselves to give us REAL women the time of day. Hurray for the millions of REAL people in this world. They are SO much more attractive and interesting than the supermodels! ( :

  3. Oh Keith your statement is untrue on so many levels. First of all, a woman wouldn’t approach a man who was “supermodel material” because he is probably ridiculously infatuated with himself and comes with a super douchebag ego to boot. Not to mention that guys that are that pretty usually go for your size zero, implanted, nose jobbed trophy wife who can’t string 3.5 relevant words together, so no average or even above average chick stands a chance with him.

    Not to mention that not all women like their men pretty. I happen to find most male models in magazines too manicured and effeminate for my taste. I happen to like my men rugged and scruffy, with a relatively healthy body. Don’t need a 6-pack cause I like me a little belly pooch. Much nicer to hold on to. 🙂

    Don’t generalize and say that all women would only approach some drop dead gorgeous, untouchable man. I’d be much too afraid that he’d look down on me for falling short of the so-called “supermodel ideal.” No thank you! I would rather approach a real man with flaws than someone who looks like he just walked off a Calvin Klein photo spread.

  4. Women will never approach a guy unless he is super model material. So us average looking guys are f…ed

  5. ^ I knew it! It’s very rare for a women to get competently approached. Drunks, creeps, and hesitant Mr. Nice Guys make up 9 out of 10 of the hittings-on that women get.

    If you have a basically normal appearance, basically normal social skills, and the nerve to approach a stranger you like, you place yourself in a very attractive minority. Whether you’re a man or a woman.

  6. Johnny, glad you put this out there. I always hear that men are hunters but I must say I don’t see many of them chasing, really. Or maybe they just don’t chase me even though I’m attractive, apparently. Because I’ve never ever had a guy come up to me unless he was terribly drunk. So I started chasing penis myself. If I spot somebody that looks nice and cute I will go up to them and let them know they intrigue me. So much fun! But so far I have only managed to somehow pick the taken ones. Maybe my next victim will be single..

  7. I appreciate the encouragement. I think we ladies need to take matters into our hands more often, instead of just waiting around. Not sure I buy the idea that men are wired to make the first move, they’re just trained — but I think the advice to be direct and confident is spot on. It’s worked for me the few times I’ve been courageous enough (i.e. drunk enough) to go for it.

  8. Busting a move is a huge rush that most women deprive themselves of. Of course, it’s a rush most men deprive themselves of too.
    Think asking someone out is so easy for men? If only you knew how many crushes we dudes let slip away because we’re scared to put our egos on the line, scared of being rejected or ridiculed, scared of being labeled a creep…

    Very few people have the balls or labes to approach someone they’re attracted to – hence internet dating. But man, once you screw up the nerve, it’s incomparable fun.

    In fact, taking that fear of making a move and turning it into a thrill has been key to my romantic success. I’m luckier in love than most people I know, and it’s not because I’m super hot or rich or anything. It’s simply because I think it’s fun to chase skirt.

    I’ve tried to explain this to lonely hearts of both genders, but the fact is most people just won’t ever do it. They’d rather wait and let love come to them, which can take a looooooooooooooong time.

  9. I’d say Married Bisexual guy’s advice applies to both genders…I’ve been on a bunch of dates where I wasn’t really aware of the fact that it was a date..And we are all nervous about it…which is why I usually say yes if someone asks me (properly!).

    My advice: Say the word date. (But wrap it into an actual sentence that concerns the two of you actually going on one.)

    And men are wired to make the first move? I practically had to attack my boyfriend to get him to kiss me – we’d been on two dates and known each other for months and I could tell he really wanted to, but alas he didn’t. SO maybe I’m just aggressive or what ever, but I’ve been the first mover a gajillion times…and it’s always awesome/terrifying.

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