Today I am answering a few common questions that come up among women over 50 who are dating.
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Dear Lisa,
Being a woman over 50 heading into the dating world for the first time in a long time, is it ok for a woman to ask a man out for a first date?
Thanks so much! Phyllis
Dear Phyllis,
Great question. For the most part at our age, it’s better to let a man do the asking. He will be flattered if you ask him out but it usually fizzles because in reality, men like being the one to choose you.
You can let him know you’re interested by winking or flirting with him online. In person, try and catch his eye then smile for about 5-10 seconds – which by the way can feel like an eternity!
If a man’s interested, he’ll get the hint and think its safe to approach you either online or in person. If he doesn’t, it’s in your best interest to move on because ultimately, you want a man who also wants you.
Dear Lisa,
My date with a guy I met online went well. I wasn’t that keen on him but was willing to try a second date since he seemed nice so we swapped cell numbers. But he suddenly postponed our date the morning we were due to meet citing work problems as his reason for canceling. He never got in touch again. Did I do something wrong?
Bridget
Bridget,
You mentioned you weren’t that keen on this man but you were willing to give him a second chance. Men do seem to have this sixth sense about what we’re feeling about them. There is a good chance he picked up on your hesitation and talked himself out of the date fearing rejection by yet another woman.
If you like a man and want to go out with him again, be sure to let him know how much you appreciate him arranging the date you’ve been on. During the date, encourage him with lots of questions and smiles. Be fun. Be flirty. If he brings up a second date, be enthusiastic and let him know you are looking forward to seeing him again.
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Dear Lisa,
Not sure about this dating rule and am hoping you can answer this question – who should pay for a first date?
Liz
Liz
The person who does the asking should offer to pay. If you are the one to ask a man out then be prepared to pick up the check. Although more than likely, he will do it. If he asks you, 9 times out of 10, he will pick up the check. My rule of thumb is to let the guy pick it up for the coffee date, the first and the second date.
After that, it’s ok to start offering to pay – whether it’s a dinner out, a dinner you make, or popcorn at the movies. If he can afford it, he will say no, I’ll get it. But if he’s like most men these days, he’s been financially wiped out by his divorce. He will be grateful for your help so the two of you can do more together should the relationship progress.
We need to start a club. I've worn Wacoal for quite a few years now. They keep my 38F girls in place. Pricey but they last and I need the support.
Lisa, Thanks for sharing. Yes! I’m still quite old-fashioned and always feel that a man should do the asking for a date.
You are welcome Marian.
It is a new world out here. I have asked men about this question. Some say they never know when to ask a woman out and are pondering the idea and would appreciate if women speak up and ask them out. It might surprise you if they are interested they react favourably. Take a chance, what do you have to loose? Either another night with the girls or alone or the possibility of an evening with a man of your choosing.
Who invites whom. I think after 50 it irrelevant. I tend to attend many events so say things like I will be attending a Hallow e’en movie and party at the Park care to attend with me. This way the man has an out he can say no, or I don’t do parties but ask me again, or no but we could do dinner some time if you like. This works for me. This way you are able to attend things you like to do with or without him. If they do go then you can see how they react around you, in your environment.
For me I find coffee meet up are more like job interviews or being on a one on one radio interview. I go away knowing there past but little about how they react in public.
That’s great that asking a man to an event has worked so well for you. Have you found it goes anywhere after the event?
I agree coffee dates can be like a job interview. The interview happens when we go into a date trying to figure out if he’s a mate within the first 15 minutes. You can take the pressure off this meet and greet by viewing a coffee date the same way you would as if you were meeting up with a new friend. You’d have fun….get to know each other…share stories…laugh and see if this new person was worth meeting up with again.
Answer to Lisa regarding my previous posts. After the event of my choice date I suggest the second date to be of his choice as to get to know where his interests lay. This way we both get to see the other in our element. So yes it works for me as it expands both of us equally into things we have not experienced yet. Some examples are going out canoeing, to the Royal Ontario Museum to see Dinosaurs, different culture restaurants all enjoyable but would not have been something I would have thought of.
Being on several coffee dates, my experience is you sit uncomfortably across the table from a man you have never met and are expected to create the fun and laughter. The men want to be entertained by you for the price of a coffee. In my experience this is difficult and a one way street on the first date. They are either talkers who don’t listen or silence who don’t speak in this environment.
Even if you even have a salad you have silences to think. A quiet moment where he can speak what is on his mind. Does he pick up the check for a light meal? This in my opinion speaks volumes. You can know right away how he felt the date went. If he is asking for you to split the check be prepared to but for me take it into consideration.
The other thing you have to consider is the distance. People who date off dating sites travel an hour to meet someone and coffee in 15 minutes seems lame. Events are more fun and shared time where you can see if he walks ahead of you, opens doors, looks constantly at other women, listens when you speak, handles the time of no conversation or needs to fill the air at every second, “these subtle things matter” in the big picture.
Hope this sheds a light for your readers.
I must be living on a different planet. I have NEVER paid for a meal in my entire life when I’ve been on a date and I NEVER will. My father always said, “It is an honour and a privilege for a man to be dating me”.
Dad passed away a few years ago. But his compliment and sage advice never went unheard. If a gentleman caller expected me to pay for a glass of wine, a cup of java or a spinach salad, I would NEVER go out with him again.
I have been divorced and unattached for a while. On average I date 2 – 3 different men a week and I’ve been having a blast. You can read all about my larger than life dating experiences in my blog/e-book. Just type my name in your browser. Comments are welcome.
To life and living it,
Ineda
The notion of never paying seems harsh and limiting. Asking someone for a date is a good idea.
What I found works extraordinarily well is to send something to the office. Men never receive flowers, you could send those. Just send something if you think you have found Mr. Everything.
Here here for taking the chance of opening up the line of communication to someone you find interesting. I would rather ask a person on a date and be turned down than to spend time wondering if it could be. We expect the same from men. Three cheers to your suggestion
I agree. I also agree with Darcy09 about refusing to pay for a meal may be harsh and limited. But this is my comfort level. If I have discovered someone interesting enough to warrant a continous dating stream, I would take the initiative and ask them out. And depending on the circumstance at hand, perhaps offer to pick up the tab.
To life and living it,
Ineda
I’ve mostly followed the “who initiated the date.” I have also found that relationships seem to work out better when he’s the initiator – maybe guys over 55 were wired that way because they were brought up in a more traditional world.
Then once the ice is broken or thawed whatever feels comfortable seems to work.
However, I don’t hear that many longer term relationships happening when the woman had more initial enthusiasm. I’m curious about what the rest of you think about that.
Great observations Dianne and very true for men our age. Thank you