Go pick a man up. I dare you!

by mssinglemama on April 22, 2008

It’s Spring. I’m feeling frisky … and I know you are too!

So… I dare you to ask a guy out.

If you’re like me and the idea of going out on a date makes your stomach squirm, then you get a reprieve. It’s only been one week since my break up, so I get to take a time out. As for the rest of you – how long has it been since your last date? If it’s been a while – then why aren’t you out there?

I know it’s a huge pain in the ass to date … but don’t you miss it? Are there any guys you have little crushes on? Could the feeling be mutual? Find out. Ask him. Put yourself out of your misery and just do it.

If you read my blog regularly you know I’m a huge advocate of women taking the plunge and asking men out, flat out

Here are a few little tid bits on asking men out.

1. Men love being asked out, it’s flattering.

2. (If they’re actually single) they rarely say “No.”

3. You seem confident and sexy.

4. You have nothing to lose. At the end of the day you know one way or another whether or not he likes you. Peace of mind is priceless.

5. Your gut is rarely wrong. If he’s been flirting with you or just smiling at you in the coffee shop, he’s probably into you. He’s giving you the green light.

6. Men are lazy when it comes to romance. They prefer it if we do the work – and that includes asking them out.

So I’m daring you all to ask someone out, a stranger, a friend or a crush…here’s how:

Find a common interest through conversation and then ask him if he’d like to join you the next time you go (insert activity here). Offer him your number (don’t get his). Then the ball is back in his court.

See? Easy as pie. Do it! It’s Spring! C’mon!

»So where are you going to find them? Read my Top Spots to Meet Men

{ 8 trackbacks }

Thursday Thoughts « Qtmama’s Weblog
April 24, 2008 at 10:05 am
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Pass the man blinders please. « Ms. Single Mama
April 24, 2008 at 9:23 pm
Oh me, oh my. The sparks are flying. « Ms. Single Mama
June 18, 2008 at 10:04 pm
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November 28, 2008 at 7:57 am
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December 12, 2008 at 6:54 pm
Too Personal? | Single Mom | Single Mom Blog | Ms. Single Mama
February 9, 2011 at 10:32 pm

{ 23 comments… read them below or add one }

Jim Everson April 23, 2008 at 9:21 am

On behalf of all of the men I know, THANK YOU THANK YOU THANK YOU for this post.


Shannon April 23, 2008 at 12:21 pm

Oh no…it’s a dare. I usually can’t resist a dare. But unless I want to go back to being a single mama again really fast, I better not take you up on it! I’d have one of the shortest marriages-three months!


jon b April 23, 2008 at 12:40 pm

My girlfriend actually did htis as well. She pursued me from day one. I was dating someone (not exclusively) at the time but had enough time in to not see other people. She kept waffling over the issue, and when my girl started pursuing me I played hard to get (which made it all the more fun) and after three weeks of this, once we went on our first few dates the sparks were already flying. It’s funny, I look back at our earlier e mails and myspace messages and die laughing at how much flirting was going on.


QTMama April 23, 2008 at 1:20 pm

Dammit I was behind a cute man in scrubs today at lunch. I lost nerve as I am having a rough hair day. 😛


jon b April 23, 2008 at 3:08 pm

QTMama never hesitate. You just lie. Yes, I said lie. Say “Nevermnd the hair, me and a couple coworkers through the pigskin around since the weather is so nice.” Bam. Hot chick, wind blown hair, football. Sign me up. Trust me.


Ronny February 5, 2015 at 2:56 am

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mssinglemama April 23, 2008 at 5:07 pm

So nice to hear from the men on this one!

Funny because this afternoon Benjamin and I were taking a walk and we saw a super hot firefighter. He invited us to play on the truck, etc. But I just couldn’t ask him out. Not flat out without a reason. They had to run anyway … but he did invite us to come by the station anytime to play with the hoses!

Ummm… definitely on the books for next weekend, just hoping he’s there when I go.


America April 23, 2008 at 8:54 pm

I had a friend mention that he likes hiking in the same canyons I do back in the fall but life got busy (and with the short days it was more difficult to get out). So out of the blue I asked him to come with me last week. We’ve been on three hikes in 8 days (we both live right on the canyons so it is easy to grab a quick 90 minute hike in the evening) AND we went to Earth Day in the park. Now I have to figure out how to ask him for a “real” date or whether to wait and see what he does. I keep being surprised that it has stayed pretty platonic, but men don’t often spend that much time with a woman unless they are interested in something… So I might just have to try the asking…


mssinglemama April 23, 2008 at 9:55 pm


Here’s what I would do…say, “so there’s this new restaurant (insert name). Have you heard of it?”

Guy’s response: Yes, sounds good, haven’t been there yet either.

You: We should try it sometime…


Wait and see what he says.

And there you go…then you’ll know. The ball will be in his court and then the hard part comes – waiting to see if he bites at the bait.

If he doesn’t – then at least you know. And odds are he will, because he’ll be attracted to your confidence. We already know he enjoys your company. Three hikes! He might just be thinking the exact same thing you are … but too scared to suggest anything else for fear of … rejection. The same thing you’re scared of.


No fear = answers.


Will Entrekin April 23, 2008 at 10:09 pm


Here’s what I would do…say, “so there’s this new restaurant (insert name). Have you heard of it?”

Guy’s response: Yes, sounds good, haven’t been there yet either.

You: We should try it sometime…


Wait and see what he says.”

Man, I liked your first answer better. Can I do it?

America, I dare you to ask him to dinner. Don’t mention some new restaurant hoping he’ll take a hint to ask you– go for it!

Why this “Offer him your number (don’t get his)?” Why be half-assed? If you’re going to ask a dude out, ask a dude out. If you’re going to court a guy, court a guy. Heck, a call ain’t even necessary: “I heard about this new restaurant? Want to go out for a bite? I’ll meet you there for a drink.”

Because, seriously, “waiting for him to call” defeats the confidence of asking him out. “Want to check out this new restaurant? Great. Here’s my number. Now I’ll wait by the phone for you to make the arrangements and invite me to eat with you.”


mssinglemama April 23, 2008 at 10:30 pm

Will, I couldn’t agree with you more…you’re right. Sounds that you, like me, are an extrovert.

You know what…I think both options work.

But, I wouldn’t call my version “half-assed.” If he is responsive immediately she’ll naturally make the arrangements on the spot. But if not…then there might be some waiting involved. Maybe waiting for him to make up his mind. Every situation is different.

There’s a lot of ways each “pick up” can play out – the key is to just dive in there and do it. You’ll make your own version.


Will Entrekin April 23, 2008 at 11:10 pm

Yeah, you’re right. “Half-assed” was a little harsh. Sorry about that. I just meant going all out, but I also love your idea–that you make your own version of “all out.”

And yes, I’ve probably been called an extrovert before. Among other things.


Shannon April 24, 2008 at 9:13 am

Ooooh….a hot firefighter. Now, that’s a catch. Time for a tour of the firehouse Benjamin!


Andy April 24, 2008 at 1:53 pm

I actually busted up laughing when I read about ‘playing with the hoses.’ Why can’t I get away with this as a pick up line?


jon b April 24, 2008 at 7:53 pm

“but he did invite us to come by the station anytime to play with the hoses!”

nothing wrong with a little job related inuendo. LOL. i wirk for a natural gas company so in my single days when asked what i did, “I lay pipe.” said with a straight face, then when they giggle, hit em with the, “Get your mind out of the gutter comment.” it seems silly now, I don;t know how my girl ever fell for me, haha.

Go get em singlemama.


polisny April 29, 2008 at 6:59 pm

well, I am not sure what to say about all the comments, but I would certainly like to say with regards to your post, that no man could ever like something more than to have the woman ask them out.
I have had women ask me out, and I only say yes because I admire their confidence… not at all interested in the fact that they are not so attractive to me. I just think for a second… NO EFFEN WAY… this girl is out of the blue… just… asking me out?

whereas if we were to ask out them… oh…
whole nother story on that one!

good post ( my god, what is your name? I like to say people’s names when I add in ending expressions like this. There must be a derivative of miss single mama)…

ciao !


mssinglemama April 29, 2008 at 10:06 pm


And so glad you agree! I know I’m right about this … like you said, confidence is SEXY as hell.


davidrochester June 21, 2008 at 12:38 pm

This is so interesting … I had a bit of an argument on someone else’s blog recently, in regard to exactly this topic.

Your generosity with photos proves that you are an attractive woman — most men would consider you well above average on the looks scale. They’d be flattered to be approached by you.

But what if you’re my charming, witty, highly intelligent friend who isn’t what most men would consider, at first glance, to be attractive? She’s the female equivalent of the kind of geeky guy who is balding a bit awkwardly and hasn’t figured out yet that he should just shave his head, who is never quite correctly dressed, and who has a mildly awkward pickup line … though he’s delightful if you let him relax and give him a chance.

We all know what happens to that guy when he approaches women, right? Yeah. It’s painful to watch.

So — is it wise for just any woman to follow this advice? What if you’re the female counterpart to that guy that no woman would ever look at?


Shanel Yang July 1, 2008 at 12:56 pm


Very good point. The majority of folks are as you described, let’s say, a bit lower on the physical attractiveness scale than those who usually have the confidence to just go up to strangers and ask them out. That’s why I wrote about a gentler way to ask someone you at least have some acquaintance with out on a date at http://shanelyang.com/2008/01/14/how-to-ask-for-a-date/

These “dates” I describe are all pretty casual and nonthreatening so not only do you find out if that person is into you, you can easily shake it off if you get a negative response.

Also see my related articles: “Why Won’t He Call” at http://shanelyang.com/2008/05/27/why-wont-he-call/ and “Is She Into Me or Just Nice?” at http://shanelyang.com/2008/05/28/is-she-into-me-or-just-nice/

@Ms. Single Mama

Thanks for visiting and commenting on my site! You’re welcome to leave links in the comments anytime — as long as they are on topic as yours definitely have been. ; )


April September 12, 2008 at 9:31 am

Would love to know where to meet these men to pick up!


mssinglemama September 12, 2008 at 11:44 am
NotADad April 18, 2009 at 7:40 pm

"6. Men are lazy when it comes to romance. They prefer it if we do the work – and that includes asking them out."

Newsflash: men are not all azy about romance. They are SCARED. That's right, you're scary. They feel like you do after a rejection and have the same avoidance behaviors. Weird, huh? Men have feelings. Not just beefcake. What a revelation!

Now consider that our culture expects men to nearly always risk rejection and ask you out. Think about the odds of rejection if a man shoots high in the attractiveness stakes, unless you're Brad Pitt or someone.

There. Now do you understand?


HB April 13, 2012 at 7:34 pm

I love your website and posts – it’s helping me so much to read as I have been single for about 4 yrs with little dating adventures like yours which I read in your ebook. My son is 7 and his father is not in the picture at all. So, recently I have been getting to know a guy who is 4 yrs younger (I’m 29) and we’re in a college class together. I noticed him right away – not sure if I was staring at him or if he was at me. But, then the teacher put us in a group together and we’ve been chatting a lot since. He is not like the “bad” boys I have also gone for in the past – or always been so drawn to (same as you in your book!!!). I hope he is not anyway – and that this nice respectful shy guy is who he seems to be. I think he is. I’ve been so frustrated with him because I love talking to him and we have a lot in common but I couldn’t get him to ask me out or flirt, etc. I am kind of blind to when someone is shy and it’s hard for me to tell how much that is playing into things. So I straight asked him out to a school V-day event but it was short notice and he couldn’t go. But said he “definitely” wanted to hang out sometime – but then weeks went by – nothing. So I dolled myself up a little bit to look a bit cuter and went to class a few days ago – asked him to sit next to me to do our assignment – as he is usually across from me. Then, I decided – not to ask him out (as I believe I did that before and I am DEFINITELY not desperate – more than anything, I am CURIOUS because I felt he liked me but couldn’t get a real understanding of the situation because he is so shy). So, after talking and talking in and after class – I sent him an email and told him he looked really handsome today (that day)! I just wanted to test that out – and it worked. So after two days with no response and feeling a bit odd about sending that email – he wrote back and did not say thanks to my compliment or compliment me back (which I am glad he did not – yes I am over-analyzing – but the bad boy type would have said something about it) – instead, he asked if I “maybe” would like to go to lunch with him before class! Yeah! So he just needed a little help in asking me out. I absolutely love it when you can be totally blunt and I am that way sometimes but with him, it might be too much until we really break the ice. I’m sure it must be so weird for him that I am not only older, but have a 7 yr old child. But, I have this really good feeling about him that is very different from the lustful, wild feelings I’ve had for men in the past. I think there could be something real and it may take time…thanks for creating this site as it is helping me at this time in my life!


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