When He Asks You Out & Wants YOU To Make The Plan!

by Cherry Norris on April 14, 2016

When you meet a new man, it's wonderful!

Even better when he treats you like a princess and wants to please you!

Detail is, when he calls you up and invites you out, he asks you to make the plan!

Today's video gives you a fun, fail-proof tip on what to do the next time a man wants you to lead.

RIDICULOUS ALERT:  Gotta give you fair warning on this one.  I kinda ran out of ideas and ended up with something … rather stupid.

Even if you're scratching your head and wondering what kool-aid I'm drinking, I hope it makes you laugh 🙂

Thanks for watching and sharing this video with your friends!

Leave your comments below about how you handle a man who wants you to take the reigns.





{ 29 comments… read them below or add one }

Senait August 25, 2016 at 8:37 pm

Hi Cherry – loved your advice. A guy just did this to me yesterday, he asked me to pick a place. It's our second date and we had a great time on teh first date, which he planned. He doesn't drive – and he's 36 years old! He rode his bike to our date – nevertheless, he's a very a successful researcher so money is not the problem for him. I agreed to picking the restaurant because I didn't want to be difficult but wasn't totally comfortable with it. I think what I'm going to do is suggest a few great places and ask him to make the choice as I'd feel more comfortable if he lead. Two questions, though, can I actually just be that upfront and tell him I'm more comfortable if he leads because he's the man? On what basis can I ground that on? I mean, what if he's like "we're equal"? Then what do you do. Second question, is a guy not having a car kind of a red flag or a dealbreaker? Why or why not? Would love to hear from you! xoxo


Camille April 20, 2016 at 12:37 am

Hi Cherry,

What a good suggestion you made to let him feel like he is taking the lead, and you still get what you want out of the date. Letting him plan the date also lets the woman know how the man really feel about her as well.


Geena April 15, 2016 at 11:25 pm

Wish I'd seen this video a few hours ago. This is exactly what happened to me today. He messaged me asking when and where. I did not respond for an hour and felt so lost. He messaged me again telling me that he was hungry and waiting.  I ended up messaging him telling him to go ahead and have dinner as I won't be joining him tonight but would have a think about where we could go for coffee in the morning. He responded with "OK". I intuitively felt uneasy about deciding when & where we would meet. I meesaged him again to let me know if tomorrow mid morning suited him and asked him to let me know today, as I'd make alternative plans if he could not meet. I then mesaged him again saying that I'd love to meet him in person tomorrow, but would prefer if he were to suggest where and when. I went on to say that I'd personally love a long walk if that suited him. He didn't respond. I feel as if I've made a dogs dinner out of this. I do like this man and he has treated me really well. We went out twice before & have nessaging each other over the last few months. We have been in the same city for 3 days and will only both be here for another 4 days, It'd be a pity not to meet. Any suggestions on how I can make a save without leading? 


Carole April 15, 2016 at 4:46 pm

If it is a first meeting from the internet, then I am comfortable setting boundaries like choosing a local coffee shop for a casual meeting without me having to drive very far.  My thinking is if they aren't willing to drive the distance to meet me in my town, then they aren't worth it.  If the man and I have already met in person & he asks me for a date then I am comfortable letting him take the lead.  If he suggests something I am uncomfortable with, then I will le him know why & ask him to go along with my suggestion rather than making me jump thru hoops.  For example once a man suggested I meet him at a beach & watch him fly kites near where he lived. This man was obviously the outdoor type.  We live about 1 hr apart.  So my suggestion was we meet half way in between & have a bite to eat at a very low key place where we could have a beverage, visit & get to know each other better.  He never called back. I don't regret not going along with his suggestion since it didn't make me feel comfortable and was all about him.  Eventually, I would have been willing to drive the distance to meet him & go along with watching him fly kites…but I also wanted him to meet me half way on the first date.  He did not call back.  Did I make a mistake?   Carole


Ann April 15, 2016 at 4:36 pm

Chrerry, love your fun sense of humor.  Delightful!




Laura April 15, 2016 at 2:53 pm

You're awesome and funny and this is a great tip even for those of us in relationships. Men who have been in a relationship for a while tend to say "whatever you want honey"…So I will alter this tip slightly to gently "nudge" my guy to stay the leading man which makes me feel taken care of and special. Thanks Cherry!


Prettieststar April 15, 2016 at 1:32 pm

Most of the men I meet online want me to do all the work.  They want me to drive to them too.   I refuse.  If they can't plan a date and come my way I don't bother to meet them. 


Most of them just want easy.  They text the same day let's get together so we can kiss.  


Many advise on finding someone nice?   Thanks.  


Lisa December 10, 2015 at 4:49 am

Hi CheRry,

This is a topic that has been on my mind for some time. I am dating this guy for 4 months now and he has never made the plans for us. He always asks me when and where, even if it was his idea to see me. I find this extremely frustrating because I feel like it is so easy for him to say he wants to see me but puts no effort into what we could do together to have a great time. 

I might add, he does not drive (@ age 27)!! This is another frustrating thing that might factor in why he does not choose where we should do. We don't really talk about the fact that he does not drive yet. Personally I think that should not stop you from suggesting what we could do together. I just think he should take the lead as a man, especially since I am already the one driving us there. 

Could you please give me a suggestion as to what I should do about this. Thanks! 


Nai`a Newlight July 21, 2014 at 9:39 pm

Aloha Goddess!
YES, Iʻve met my dream man and weʻve just completed his one-month visit to me in HI (he lives in FL)!  Mahalo for all your invaluable advice.  My man really prefers me to lead (he says alpha females are exciting), which I gladly do, as weʻre on MY turf.  We meet next in DC in Sept., and heʻll have his chance.  
Love your cues!


Tina July 20, 2014 at 6:34 pm

Break a leg, Cherry!


Cherry Norris July 22, 2014 at 6:22 am

Thanks Tina!! 🙂


Tina July 20, 2014 at 6:34 pm

This guy might actually be happy going anywhere as long as he's with you! If he wouldn't even come up with choices, I'd answer, "Only if you pick next time." It's very important to me not to repeat the experience when I'm with someone who goes along with everything and then whines about my choices YEARS later.


Helene July 19, 2014 at 1:03 am

Hi Cherry,
I really enjoyed today's video.  When I had moved to a new city, I was asked out by a very nice local man.  He, like you said in the video, wanted to please me by asking me where I wanted to go on the date. I explained to him that I appreciate his thoughtfulness, but that I did not know of any restaurants since I was new in town and asked him to make suggestions for me to choose from.  He kept saying cheerfully, "Oh, I don't care, whatever you want will be fine."  He probably thought he was helping, but it was actually quite frustrating for me. 


kay July 18, 2014 at 3:19 pm

Question:  What do you do when a man is unfamiliar with the city? I have an interest from a man that lives 4+ hours away. He flys or drives to see me (and stays in a hotel) — I don't want to lead by making suggestions as to what to do, where to go, type of restaurant, activities, etc.  Please give me strategies and scripts.
Thank you, 
Handsome and younger, too!


Cherry Norris July 18, 2014 at 5:45 pm

Congratulations Kay!
When a man lives away and is unfamiliar with your city comes to take you out and asks you to make the plan, tell him you’re happy to make suggestions, then he can decide where to take you. I suggest giving him 3 choices: budget, moderate and expensive then let him decide.
Have fun!
Love, Cherry


Maria July 18, 2014 at 3:02 pm

I have had many men do this and when they can't break out of this too nice persona I have actually dumped them. If you really like them I would suggest making a day all about them. Tell them you want a day all about them and make it a fun flirty kind if thing. They pick what you do, the place, and reassure them that this date is all about them and your happy just spending time with them. Be proactive and make the day all about them by listening and going along wiht what they like and want. If the man can handle this and let the day be all about him then he is a keeper. If he can't and he is still infatuated wiht pleasing you he may be too good and you may need to find someone else who has a little back bone.


marcia corenman September 14, 2013 at 4:18 am

This happened to me the other day on the second date! Somewhere in the back of my mind I knew I didn't feel comfortable naming a place. His excuse was that he'd like to come to my neighborhood and because he was unfamiliar with the area could I pick where to go. I said I didn't feel comfortable naming a place because I had no idea what kind of food he likes or the type of place he would prefer. I told him about a few places from fancy to simple and suggested he make the plan and that YELP may be a good resource to help decide what he'd like. He came back with a place and time. It wasn't anywhere I'd ever been before, it was simple but tasty meal. Success! He lead, I followed! Marcia


Cherry Norris September 14, 2013 at 6:04 am

Yay Marcia! Well done 😉
Love, Cherry


Jasmin February 2, 2013 at 10:47 am

Thank you so much for answering my question, Cherry. I'll try that next time my boyfriend asks me out – yes, I'm so happy that he's my boyfriend now! We just celebrated our second-month anniversary a few days ago and our relationship is going great.


Cherry Norris February 2, 2013 at 6:27 pm

Yay Jasmin!
Sooo happy for you 🙂
Love, Cherry


Janise February 2, 2013 at 1:16 am

Sometimes men plan dates as surprises and they are not always things I am comfortable with. For example on that show The Bachelor he takes women sky diving, bungie jumping or rock climbing, helecopters scare me and so does horback riding smelly animals… For me that is not my thing and feel very uncomfortable doing such things. I don't feel like I need to prove how tough or brave I am for him to like me or even be his bootcamp buddy on a date. Soooo not romantic.  I am very  outgoing in other ways though so I am not a party pooper but those things could be life threatening. I love life to much to risk it doing stupid things like jumping off a building.  How does a gal tell a guy who has set up such a date that its not cool with her without making herself look like she doesn't know how to have fun or insult his idea for the date?


Janise February 2, 2013 at 1:19 am

I meant HorseBack riding not horback riding. I am a respectable gal.


Bee February 2, 2013 at 5:59 pm


"I meant HorseBack riding not horback riding. I am a respectable gal."
And you have a good sense of humor too!




Cherry Norris February 2, 2013 at 6:28 pm

Ladies, I agree 🙂


Dianne February 1, 2013 at 11:39 pm

LOVE your videos Cherry!!  Was very glad to hear that your solution was the same one I came up with for the same issue with my boyfriend and I can confirm it works really well – now he brings me a few options and I choose and we're both happy  🙂
What show are you directing in Hollywood?  Would love to see it and hopefully meet you.


Cherry Norris February 2, 2013 at 6:35 pm

Thanks, Dianne!
So happy to hear you’re both happy!
The show I’m directing is “Here’s to Love” at Anthony Meindle’s in Hollywood.
… scenes of very funny dates! (lol)
Thursdays Feb. 7 & 14 at 8:00
RSVP: 323-993-7113
Would love to meet you there!


Suzanne February 1, 2013 at 8:43 pm

Hi Cherry, Funny video, as always…You are just too cute!! When this has happened to me over the years, I usually throw out a few things I like, things I like to do & something I'm in the mood for & then ask him to use his imagination to connect the dots…Over the years, it has made for some REALLY fun & interesting dates…(and some kinda weird ones too…lol)….Never a dull moment & the guy is happy that he was given a few clues to piece together & come up w/something really unique! YeeHaw…saddle up cowboy!


Cherry Norris February 2, 2013 at 6:38 pm

You go cowgirl!! 🙂


Newcomer February 1, 2013 at 7:12 pm

Hi Cherry,
You're horse ride was adorable and I LAUGHED out loud!  And congratulations on directing! 
Sometimes men don't know what they're doing.  By that I mean, the man mentioned in the letter doesn't realize he's asking her to lead and he's setting himself up to bond less to her. So for her to just say, "I'd like you to lead…" that will get his attention, great advice. And it gives him time to process this and figure out if he can or not.
One other thought is, from reading Pat Allen whom you've referenced as well, he may really be a Beta male or a boy.  Guys are trained to initially pursue and even boys or Betas will do that but as time goes on their true nature comes out and they may really show they want to be pampered, are Beta or is an immature boy?  He may be feeling comfortable in the relationship and he's revealing his true nature?
So it's great she's stating it and he'll either rise to the occasion or he may not really be ready to be a man or leader?
Happy Friday to all!


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