He Invites You Out, Then Asks You To Pay!

by Cherry Norris on March 18, 2015

You finally get a date with a new man you're excited about!

Who fortunately takes you a great place place you really like!

And everything's going swimmingly … nice conversation, good cheer …

Until the check arrives.

He reaches in his wallet and takes out his card, then asks how you'll pay your share!

Today's Video shows you what to do when a man invites you out, then asks you to split the bill!

It's a Jaw Dropping experience. Especially since he's the one who invited YOU!

See how to handle this situation with grace and ease … while keeping the possibility open for love and romance.

Enjoy and leave me a comment below!

Love,

Cherry

P.S. Watch What To Do when a charming new man throws down his cash and asks you to pay your share!!

{ 51 comments… read them below or add one }

Amanda May 17, 2017 at 7:35 pm

Been out with this guy a few times.  He always paid.  I invited him to lunch one day , my treat.  Yesterday he invited me to dinner when we got up to pay he asked whose turn it was to pay.  I was stunned.  I feel if he invited me then he should pay.  Which he did.  But should I take this as a warning sign?

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Erin September 22, 2016 at 7:16 pm

I met a guy online, he wanted to meet pretty quick to see if anything was really there. He invited me out for drinks and I told him I couldn't afford it. Meaning I didn't expect him to pay for me. So I get paid the next day. Figured I could cover at myself if he asked again. He asked me out for breakfast and I agreed. He however, expected me to pay both shares of the bill, after I drove an hour to meet him (he drove 5 minutes). And I've clearly stated to the guy before hand I couldn't afford to eat out and have drinks often. Then he sticks me with the entire bill and didn't even offer to cover the tip. My mom taught me if the guy insists on paying you should at least offer to cover the tip. Was I wrong for not wanting to date the guy?

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anne July 12, 2016 at 9:30 am

HI,a man asked me out on a lunch date yesterday i had a sandwich and a soft drink,when the bill came he asked me to pay for what ive had i did but i dont want to go out again with him .How do i tell him up not happy with him because of this

Thanks

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toni fagbure December 5, 2015 at 6:23 am

Hi cherry, just met this guy online and on the first date he asked me to pay for the 3rd round of drinks. I was dissapointed, but i didn't give up. Then i kind of messed up and was over an hour late for a date. He got angry and thought i stood him up so to apologised i offered to take him out. He gradly agreed and i paid a lot of money for dinner and drinks and he was happy to order what he liked after this he tried to get out of paying for a shot by having a bet and i lost so he made me pay for another drink. I think he is selfish and though i like him i can't deal with that so i am cutting him off.  am i correct in doing that or should i talk to him about it?

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Joana April 3, 2015 at 1:55 pm

Hello Cherry! It's great when we can speak our truth like you showed in your video. Before I learnt your tips I thought it was right to share all bills with men, totally overlooking my true feelings of wanting to be nurtured and protected. Best of all, most men like to be nurturing and protective, and this is why I am beginning to really admire men.

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Cherry Norris April 3, 2015 at 7:12 pm

You got it Joana!  Well done πŸ™‚

Love,

Cherry

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randy March 20, 2015 at 11:14 pm

From a guys point of view the flaw with this thinking is that it's actually dysfunctional to set up a first date as romance.  It's best to keep it first as friends to see what you have a solid connection as friends first.   After determining after some time if the friendship potential is solid, then you can take it into romance and it's fine for him to pay.  Paying at the beginning establishes the wrong message!

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Lisa March 23, 2015 at 1:44 pm

except that in the overwhelming majoriety of cases, guys dont ask women out on dates because they are looking for a friend. IF in fact a guy is not interested in a woman romantically, THEN asking her out and paying for the "date" sends the wrong message.  again, this is almost never the case.  

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Laura January 30, 2017 at 10:15 pm

Seriously, dude? If that's your mentality, I'll bet you're still single! Guys like you are what is wrong in the dating world these days. What happened to being a gentleman?

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Bren March 20, 2015 at 2:57 pm

I have never paid and refuse to pay on a date.  if he invites me out and can't or won't oay….loser, no gentleman.    I would like to know he can be a provider even though I take care of myself. If we date often or become a couple, of course I offer every now and then.   I have not  been out with guys who quibble over a coffee date pay…..why the heck do I need that? No pay, no stay and I am no gold  digger. But I am a character digger.    I don't Ever pick the most  expensive, I always consider the guy. Some are pigs, some are gentleman. Generosity, class and kindness talk loudly to me. I am not that desperate to be with someone who is mean ass from get go.    I am technically interviewing him as well for character. If they tell you who they are at the start, believe them….AND WHY WOULD  YOU WANT TO DATE A JOBLESS GUY? No. I am like it when he offers and pays first. I never offer if he invites me. I usually do coffee if he likes he, he suggests a meal…..that's my sign…..he s paying……if he asks me to pay, which has never happened, I leave……..via the restroom…..

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Charlene January 10, 2015 at 1:12 pm

Wish I would have known this before – critical info.
Spent 3 years with a guy – only had honestly about 3 or 4 actual dates in that time period with him. The rest of the time we spent at his house
watching TV. I was dumped after 3 years.

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Leslie August 13, 2014 at 2:23 pm

Cherry,

I need help!  New to dating scene after being married for years.  I was invited out by a man, via online dating site, to a nice restaurant.  Well, I assumed we would get something to eat.  When I got there he was at the bar, no problem there but I sat down and for 1 and a half hours he didn't ask me if I wanted anything to drink (I ordered water to start).  I was starving having not eaten beforehand.  I really got the sense he didn't want to buy me a drink or anything for that matter.  I left thinking this was a red flag.  I think he at least could have asked me if I wanted anything.   I ended the evening and he said he wanted to see me again but I have mixed feelings about his concern for my comfort and his generousity.  

Can you help me.  If a man asks me out to a restaurant should I ask if I should eat first or is it assumed we will eat or have a drink?

Leslie

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Goldberry April 22, 2016 at 5:47 pm

For the record, this happened to me once as well.  He kept wanting to order more and more wine even though he'd invited me out for dinnertime and we hadn't eaten.  I finally told him I couldn't drink any more on an empty stomach, so we got some food.  At the end he was very glad for me to pay the tip.  I shouldn't have offered.  He had a drinking problem and was very selfish.

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Andie July 28, 2014 at 10:21 pm

Dear Cherry,
The discussion of "who pays" and "when it is the right time to have sex" come up inevitably and your short sweet clear concise videos are invaluable resources. I have a positive story to share. I have joined Tinder–talk about quick , easy and it's raining men!  
Here was what a man wrote: "let's meet at 7 pm, (said location). As it's a tinder date and a first date in this day and age I'm sure you'll appreciate it will be Dutch.
My response: "I appreciate you addressing this in advance, thank you. However, I am old fashioned, and my experience on Tinder has meen that men invite me out pay for me and are happy to do so. I am seeking a romantic relationship not a friendship." Andrea
His reply: "Happy to meet you for a coffee and I will of course buy the coffee or tea. Are you free Wednesday afternoon?" 
When I didn't respond right away.."And if we hit if off, I would be very glad to take you for a lovely pub lunch my treat."
My response: Hi, __ thanks for understanding. Coffee or tea sounds lovely and I am indeed availalble Wednesday, look forward to your plan.
His "Impressive. 3pm ___ place."  
Cherry your work is indeed retraining!!! Many many thanks and lots of love, Andie!! xxx

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Cherry Norris July 28, 2014 at 10:37 pm

Well done, Andie πŸ™‚
Love, Cherry

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anonymous March 17, 2014 at 5:18 pm

He traveled over 2 hours to come on this date. After the meal, he asks if we can split. I do so graciously. I understand he’s not working and all but it did make me feel less cherished. I wondered if he just saw me as a friend or if he liked me as a partner. However we’ve maintained contact since then and honestly he’s been a real gentleman. What is your advice.

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Cherry Norris March 17, 2014 at 9:46 pm

My advice is to keep seeing him as long as it feels good for you to do it!
Love,
Cherry

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Nelly Mentor June 22, 2013 at 4:33 pm

A 'great date' doesn't a gentleman make. Women should exercise their discretion when assessing romantic candidates, the same as men do.  
If the guy invites you out and then asks you to pay, do so with the intention never to see him again. A lenthy discussion about how it makes you "unconfortable…" I don't see the point.  
Some men choose not to pay for the woman's share on the first date because they decided that they're not interested in seeing her again. Their gesture is meant to be insulting.
So why bother being that vulnerable with someone like that on the first date?  If the woman really likes the man and he invites her out again, then maybe she should say something.
A spiel like that is too much investment for a first date, imo, particularly someone she had met online.

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Cherry Norris June 22, 2013 at 5:37 pm

Hi Nelly,
Appreciate your comment. The point is practicing with men you’re not interested in prepares you for the one you are. You’re not responsible for a man’s feelings or his gestures. This is about knowing how to take care of yourself.
Love,
Cherry

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Ninah June 22, 2013 at 3:40 am

I've been dating 30 years.  If a guy doesn't pay for the first date, that tells me that he's not interested in pursueing dating further or just wants to be a friend.  If he really likes me, he will want to pay to keep me.  This may sound selfish, but really it's not.  It's more about seeing if he can follow through or is looking for a mother-figure.
I have found that the man who doesn't have much money, will plan a first date where he doesn't have to pay, like riding bikes, or hiking in a park.  Then he'll tell me his financial situation (which may or may not be true), but if he's interested, he'll take me out again, this time he'll pay – even if I offer.  Really.  From that point on, if the chemistry is there, we'll negotiate.
So, if a man is interested in me, he'll lead.  If I'm interested in him, I still let him lead.  This doesn't mean that I'm a servant, but rather I become the prize, who recriprocates also in different ways (i'm not referring to sex here, but compliments, noticing his needs, remembering what he said, etc.).  Men think more highly of themselves when they can be the provider/protector  This way, we're on more even footing and can have a better chance of having a good, more balanced relationship. .  After all, isn't that the point?
 

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Marta S. June 22, 2013 at 1:48 am

Hello Cherry;
The worst dates I had were when the man expected me  to pay both his share as well as mine-he's long gone now, and a man who asked me out and then expected me to pay for his iced tea and mine too. I  only had money for my drink, so I drank water and he's gone too, I have yet to meet the generous bells and whistles man who pays for his share..and no deal breakers either.. Guess its time to figure out my next move-literally, and hope that things fall into place in a drier easier to navigate location..

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Michele June 22, 2013 at 12:54 am

Awesome advice.  I appreciate your wisdom, and this makes purrrrfect sense!

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Kara June 21, 2013 at 3:42 pm

I am five years single, dating – At first, I would worry about paying on a first date..or meet/greet.  Now, I limit the "meet/greets"…move it to first date stage and I do not worry about paying (nor do I offer).  Most men "get" that I am dating to find love and would never ask (because that is the vibe I am giving). On the rare occasion that someone would ask, I would pay my half and for sure would not accept another phone call. Asking for a woman (who ordered reasonably- one drink, one food item) to pay is classless and I would offer NO excuses for that man.

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Ginell June 21, 2013 at 8:16 pm

Bravo Kara! I'm also looking for love and if I get asked to pay on a date, you can rest assured that this will be the last time I see him

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Louise December 14, 2012 at 8:22 pm

Hi all,
I know this post is month's old but I couldn't help contributing. As a student I once went on what I thought was a date with a lovely marketing fellow I met thru an ad. He took me to a wine bar and he paid for two glasses of wine. It was so delicious we decided to have more. So we went through the menu and I thought I should get the next round as he paid for the first. I asked 'shall I get a bottle or two more glasses?' He replied ' a bottle.' I hung around so he could see the prices. He made no move to contribute, not even £5. I forked out £15. This is a man who pays £1000 a month for a room in a house, plus bills seperately on top. I was floored. He didn't call me back after that drink and I wouldn't have seen him again anyway.
Fitteen years later, I certianly would handle that differently! Louise

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lady dee May 30, 2012 at 7:24 am

Cherry,
I agreed to go on a date with a man who contacted and persued me on the internet.  He indicated he wanted to split a salad and entree and allowed no input as to what I'd like insisting on choosing both courses for "splitting".  He then brought up a professional and lovely MD with whom I do business and told me of how on a date she asked him to return to her hotel room following dinner for sex.  He was so disrespectful in that he shared this intimate detail about a woman I admire and had the audacity to say he was not attracted to her and rejected her. Horrid.  When the check arrived he asked if we should split it, and I said "no", I don't think so.  You suggested we go out, I'll allow you to get it!     
I felt that he was uncouth and rude so I felt no obligation to split a check with him… In the best of circumstances I would have been put off yet this was unforgivable in my book.  

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Sharon Turby December 22, 2011 at 4:47 pm

Cherry,
I believe a man who asks you out as a date or a friend should at least offer to pay the first time. Then after that they should establish an agreement or negotiate how this should be handled according to whether the relationship is a dating situation or a friendship in verbal communication.
Sharon

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Kate December 21, 2011 at 2:13 pm

Cherry,

I just wonder if I would be able to say what you suggested in the video with a guy I was with on a first date. It would be very exposing indeed…. Do you have examples of women who have done as you suggest here?

Many thanks! Kate

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Anthia Ashe December 18, 2011 at 9:15 am

Hi Cherry,

Really good to get real life experience questions! And good answers. Thanks. Anthia

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Shiva December 18, 2011 at 2:04 am

The first time I go to meet a man I’ve connected with online, I consider it a “meet and greet” NOT a date. If he were to invite me out after our initial meeting, that is a “real” date and I would I would like him to pay!

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Cherry Norris December 18, 2011 at 3:38 am

Great perspective, Shiva!

Thanks for sharing.

Love, Cherry

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Lorene December 17, 2011 at 10:35 pm

Cherry, the words you give us are a beautiful way of letting that guy know that he’s messing up. It gives him an opportunity to learn from his mistakes! And then I’d feel better about having spoken up about my unease, no matter which way it goes.

Thank you,
Lorene

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Temille December 17, 2011 at 6:03 pm

This is a clear sign that a friendship is in progress, not a romantic interest. I remember once being so embarrassed when at breakfast with someone really special to me who had to leave early; left money in the folder on table that I opened to leave another tip for the Sista from Ethiopia who had been so gracious, and discovered he had only left money for his breakfast! Imagine if I had walked out, assuming the bill had been paid in full? What a wake-up call that was. We talked about it later, he apologized about not letting me know he was only paying half. Needless to say, that was our last date.

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Cherry Norris December 17, 2011 at 6:18 pm

Great story, Temille.

Thanks for sharing! πŸ™‚

Love, Cherry

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Angela December 17, 2011 at 4:02 pm

Thank you Cherry. I too have not dated for a few years now. It just seemed too much pressure. I am still hesitant to start again but your advice gives me courage to use respectful yet clear communication with prospective dates.

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Tia Dobi December 17, 2011 at 1:53 am

Thank you for responding to my question.
To be accurate – how do we uncover before the date if the man is paying or if he is expecting dutch?

The reason I ask is because
a) I want to know before I go
b) I did use the Dating Director lingo in my response (because I have Cherry’s cool products buy them now people) and the man said something about “equality” and I gladly paid (and that was the end of contact with him).

Can this topic be re-approached here?

Thank you!
Tia D., Los Angeles

P.S. After the gent left (there were no hard feelings, no body died or got upset…I wanted a minute to myself) other patrons (who, unawares to me) were watching and listening said “My goodness! You handled that beautifully” Woo hoo.

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Cherry Norris December 17, 2011 at 4:05 am

Hi Tia,

Thanks for your note. If you want to know if a man is paying before you go out on a date, ask him. Say something like, “Thanks for the invite. Just to be clear, is this a date where you are taking me out and paying? Or do you expect to go dutch?” Then you’ll know!

Thanks for the promotion!! So happy you’re learning and doing so well in your interactions with men! You handled this situation beautifully! Excellent!

Love, Cherry

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Dorothy December 17, 2011 at 1:40 am

I think that if the man invites you and cannot afford to pay for just coffee, it is a message. Run like hell! I dated a man that paid for our first date dinner and then told me that I had to pay for the play, which I did. This was not an arrangement we made in advance. At the time I heard myself say, this is a message, run, and I did not. I did not even protest, even thought I did not really feel that it was my place to pay. I was a coward then. Now I would do things differently. I want to know in advance so that it is my choice to do so or not, or to even accept the date or dot. I know that times are hard right now and some men cannot afford to date. I know one such man and he does not date until he can afford to do so. I am willing to reciprocate in the future, but if the date starts out this way, I prefer the option of declining the first date.
Thank you, Cherry, for all the great info you give us. Merry Christmas!

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Cherry Norris December 17, 2011 at 4:07 am

Thanks for your comments, Dorothy!

Appreciate your sharing your observations! Sounds like you’ve really grown πŸ™‚

Love, Cherry

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Moira December 16, 2011 at 9:59 pm

Another great one, Cherry! Thank you! I’ve been lucky so far in dating men who have been generous and protective – and now I’ll know what to do if this arises.

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Renee December 16, 2011 at 5:32 pm

Once again, Cherry – you offer such great wisdom to handle difficult situations graciously. Thanks so much! Blessings & Joy, Renee

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Tina December 16, 2011 at 4:27 pm

WoW! This was very enlightening! Thank you Cherry for tactfully teaching us how to handle a most uncomfortable situation with honesty and grace! πŸ™‚ So far I have not had this problem when dating however, I have dated a man in the past who use to drive an hour just to pick me up for the date! Is that the same thing? At times I felt bad he spent so much on gas and asked him if he would meet me half way between where we both live. He politely refused and told me that would never happen! πŸ™‚ How would you have handled that, Cherry?

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Cherry Norris December 17, 2011 at 4:11 am

Hi Tina,

Sounds like you have a real man after you! Let him come to you and don’t worry about it! You’re doing great!

Love, Cherry

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Diana December 16, 2011 at 1:43 pm

Cherry, on a few occasions I’ve been out with a beautiful young man who is broke. On his birthday when someone else had his wallet, I offered to buy him a drink, and he said, “I pay, not the woman.” He had bought me a drink earlier in the evening, but on another occasion told me he never buys drinks for women in bars. The other day when I was talking about what to get him for Christmas, he said, “Don’t spend money on me.” And he seemed sad and embarrassed about it. I’m trying to figure him out. I feel he really cares about me, but he thinks of me as a movie queen, a rich woman. I do come from that kind of background and don’t hide it, but it’s just like owning some property. It’s a thing I have, not who I am. It’s not about ME personally. I feel he cares about the riches in me personally but is intimidated by me because of my life experience and possessions, even though I’m no longer rich in cash money. What I feel we are both rich in is a very deep connection. There is a harmony between us I’ve NEVER felt before… an ease and a sense of deep understanding. I just look into his eyes and he speaks to me without words, and I am sure I understand him when he speaks to me like that. I’m going to wait it out and see what happens and let him lead. But is there something I can do to help with this financial thing? When he asks me out, I’m afraid to order anything since we haven’t had a romantic type of date yet. It’s been more like he feels privileged to be with his mentor since I am his acting coach. And I am more than twice his age and he’s thirty. Yet we are equals in this way I’ve never felt before while he is definitely the man and I am definitely the woman.

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Sue December 16, 2011 at 4:15 pm

Excellent!

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sharon December 16, 2011 at 6:39 pm

I just wanted to say I really can relate to what you wrote… I am seeing someone who is 33 and I am 52. We have such a strong connection together the age difference never gets in the way… so what i look at more is that then all the other things… do you enjoy being with him? does he enjoy being with you? is he reliable? does he provide you what you need? This to me is more important than who pays the bill but it should never be below 50/50. If a man cannot pay at all then I would certainly question his motivates… and perhaps that is exactly what you are doing. just wanted to share with you. thanks.

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Cherry Norris December 17, 2011 at 4:10 am

Way to go, Sharon!

Thanks for sharing your experience and such valuable questions to ask!

Love, Cherry

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ali June 23, 2013 at 1:02 am

Yay for Sharon dating someone so much younger. A man 18 yrs younger than me asked me out and I feel hesitant about that age difference. We have not gone out yet, but maybe it's not something I should hesitate about after all. I still have not said "no" lol and he keeps calling. thanks for sharing!

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Cherry Norris December 17, 2011 at 4:14 am

Hi Diana,

Thanks for sharing your story. There are some great questions and an excellent situation for a future Q & A! I think many women will benefit from knowing what to do in your situation!

Love, Cherry

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Sophia June 21, 2013 at 5:43 pm

Hi Diana!
The good news is he cares fo you and wants to provide for you.  He is trying to be the masculine man: provide, cherish and protect. He may be treating your non-dates as a way to be in you r life while he's building his. Please let him.  He will then be able to come ot you as a full partner.
If the conversations between you feel like mentor and devotee it can be turned around.  When Cherry did a call with Matthew and Orna Walters they spoke about how to set the tone that you are a romantic interest not a business partner, mentor or pal.  when he asks you questions about those things Cherry said give a nice brief answer and turn it back to him – And you? Matthew kept peppering her with questions and Cherry kindly answered and kept saing, And you? 
You may have to come out and tell him, I respect you and support your quest or drive to do (fill in the blank) but I don't want to be your mentor. 
The only red flag I'm sensing is you feel on an equal leve with him but he may not with you. He may feel beneath you. So when in acting class coach him.  Outside of acting class let him rise to the occassion of being your masculine man.  And be a little cautious of falling in love with his potential.
Hope it goes well, yu sound like you really care for him!
Just my thoughts?
Sophia

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Ziji December 16, 2011 at 12:38 pm

This is a very useful supportive video for those like me who haven’t dated in many years and need some protocol for sticky situations. I must admit that in my way-back-when dating, that issues never emerged. Still, it’s a different time in the dating world, and I’m happy to
have your tips. Thanks!

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