Just Jill is the creation of Jill Cohen Morris. Jill is an avid Rambler and married mother of two from Toronto, Canada, with a remarkable zest for life and a fabulous sense of humor.
Dear Just Jill,
Help! I'm about to cross the line from friendship to romance, and I am freaking out!!
I’m in my late fifties, divorced for two years, and nothing romantic or sexual for almost ten years. Enough said.
I’m a mess … forget about sex, let’s talk basics …kissing… I am not sure if I even remember how to kiss?? What if I break out in nervous laughter?
I really, really like this man. We have spoken on the phone, gone for walks, had coffee, and been out for dinner twice. Now he wants to make me dinner.
Where is my confidence? Why am I so nervous? I need advice from my wise Sole Sisters. How do I calm down? How do I enjoy the moment and stop overthinking?
What’s a gal to do?
Sincerely,
Panicked Pearl
Sole Sister Advice & Comments
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Just lean in and go for it, laughter is fine and fun. Enjoy! You have much more restraint than me.
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He’s likely more panicked and more nervous than you. Imagine him writing in his journal how he feels like a school boy asking a girl out he REALLY likes. Show a middle-aged man a middle-aged woman he likes, and I’d be prepared to bet real money he sees the beauty and not the ‘faults’ that women have been trained to focus on.
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I have been in your shoes! It’s like riding a bicycle but more fun!
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I’d be a wreck, I’m sure. Vulnerability is courage. Be brave. Be bold. Be you.
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Relax. Maybe do something beforehand to take your mind off of it.
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What an exciting adventure for both of you! It is ok to giggle nervously, and it’s ok to let him know how you are feeling (in fact, I recommend it). I did the same thing a few years ago, and it was the best thing I ever did. Enjoy yourself and let everything unfold naturally
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I’ve been in these exact same shoes, same timeline. Try to relax. Don’t be afraid to express your feelings. And the other thing, my girlfriend asked me, and I’ll go ahead and answer it, yes, they expected to be completely shaved down there lol.
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If he is really into you, nothing you say or do or wear or whatever will bother him. It’s only when we are looking for a way out that we find faults. You are perfect just as you are for the right person!
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On our first date, my now fiancé (69 and a widower) said to me (68 divorcee) ‘You’ve got to realise I’ve got no idea what I’m doing’. It really endeared him to me as I didn’t either!
SSR doesn't endorse the advice or content shared in this column. Our goal is to access the wisdom of our incredible Sole Sisters.
READ MORE > Ask Just Jill, Rambler Cafe Blog
I feel your anxiety about going to his home for dinner! I had been dating for a decade before I met my now partner of 3 years. We have a loving, physical relationship. I had serious jitters and almost cancelled when he invited me for dinner. Going to someone’s home is very intimate. It’s also behind closed doors and not in public. Not everyone behaves as we would or how we expect them to behave. As any teenager learns, kissing can lead to more. I suggest you ask yourself a key question…Do I want to have sex with this man or do I just think he’s a great guy? If your answer is, I’m not sure, not yet, or no, then perhaps suggest dinner out until you know the answer. Desire for another person is a pretty clear signal. In my early dating after divorce, I made that mistake. Nice guy but once we had been intimate, I realized I’d talked myself into it. Of course, if we only let desire lead that can end up with bad decisions too. LOL. Take it slow, you set the pace. Listen to your gut. There really are many fish in the sea. We need both aspects for a relationship to thrive.
Just my advice from the trenches. Enjoy the journey.
I’m in the same position divorced from my children’s father. Then I met a partner who was adorable. I bought a host with them, lived with him for 3 and 1/2 years. He had a heart attack driving and passed away, I didn’t know what I was devastated. I didn’t know what I was going to do. I was heartbroken well. After so many months his friend came into my life and consoled me. He knew I was going through a really rough time so we chatted and enjoyed each other’s company. It was my support and grieving. Then we became friends and partners and we joined in as common law partners. I lived with him for 18 years. I was his caregiver for the last 5 years. He was on kidney dialysis. Well bless his heart. He asked me to call an ambulance. I called the ambulance. He passed away in my yard and the ambulance that was was November 20th 2024. So it’s been so lonely and heartbreaking. I finally met another beautiful person gentleman that I am going to start a new chapter of my life, friends, live, love and life and be positive. That’s my philosophy. Life is sure. Enjoy it everyday one day at a time
I don’t think this piece of advice has been given yet so…. I would put it on the table with him. As you are at his place for dinner just say “I’m feeling really nervous about us progressing to the next stage”. I’m sure he will be relieved to hear it and that vulnerability will open him up to be the same with you. Good luck! I can’t imagine how I would feel! I’d likely be terrified so it’s nice to be able to sit back and be the armchair advisor! Ha!
Oh my goodness girl. I can imagine and empathize with you completely! Perhaps being prepared will help you. Consider and evaluate if you have vag dryness. If so address with dr (there are lubes, bioidentical hormones that help) im sure he must be nervous too. Above all try to enjoy! It will all come back
You are so brave – all of you! I can’t even find the courage to consider dating. I’ve been on my own 10 years now and I don’t even know where to begin.
I have no advice, but I appreciate you asking the question so that I can read all of the responses. And – for the woman who said that men expect us to be shaved bare … umm, if this is commonplace, I’ll stay single then. If a man is bothered by my normal hair then he’s going to be bothered by a whole lot more of me!
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