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 out!
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!!
{ 23 comments… read them below or add one }
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!
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.
Excellent!
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.
Way to go, Sharon!
Thanks for sharing your experience and such valuable questions to ask!
Love, Cherry
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
WoW! This was very enlightening! Thank you Cherry for tactfully teaching us how to handle a most uncomfortable situation with honesty and grace!
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! 
How would you have handled that, Cherry?
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
Once again, Cherry – you offer such great wisdom to handle difficult situations graciously. Thanks so much! Blessings & Joy, Renee
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.
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!
Thanks for your comments, Dorothy!
Appreciate your sharing your observations! Sounds like you’ve really grown
Love, Cherry
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.
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
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.
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.
Great story, Temille.
Thanks for sharing!
Love, Cherry
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
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!
Great perspective, Shiva!
Thanks for sharing.
Love, Cherry
Hi Cherry,
Really good to get real life experience questions! And good answers. Thanks. Anthia
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
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