Dating Over 40: I Wish I Could See Him More Often

Melanie has been seeing John for 5 months now. Overall things are pretty good. They enjoy each others’ company and she hasn’t noticed any big red flags. Whew!

Yet Melanie thought things would be farther along by now. They spend their weekends together, but she wishes they could have dinner on a few week night as well. John seems perfectly happy with the way things are. He hasn’t stepped up their time together or requested more. She feels confused by this and isn’t sure if she should be reading any meaning into this behavior.

I reassured her that as long as John still makes plans with her on the weekends and calls frequently to talk and stay connected, there probably weren’t any issues. We could go on for days trying to read meaning into his not seeing her more during the week. You know how that is. We can create reasons why he’s not that available such as:

  • Maybe he needs a lot of alone time.
  • Maybe he’s tired.
  • Maybe he’s not that into her.

But what if, maybe he doesn’t know SHE wants to spend more time with him?

Melanie is a very busy woman. She takes yoga two nights a week, goes to networking events and does volunteer work. Maybe she’s trained him inadvertently that she is too busy during the week. So he has no idea that she’d like to see him more.

Solution? TELL HIM!

I suggested to Melanie that she say something simple like, "John, I wish we could see each other during the week too. We could have dinner, take a walk. or share a glass of wine. What do you think?"

Isn’t that simple?  Chances are very strong that John would be open to getting together on week nights. But at the beginning of their courtship, John had asked Melanie several times to see her and she was always busy. He’s a nice guy and can keep himself entertained. So he followed her lead and kept his time with her to the weekends.

In addition, Melanie has this idea that the man has to lead all aspects of the relationship. This is absolutely not true. In fact, many times it’s the woman who will move things along to ask fro a commitment or discuss marriage. Of course this is not advisable during the initial dating phase, but once you know you have an unspoken date on Saturday night, you have moved into the relationship phase. Completely different rules apply.

Some might argue that things might be a bit touchier for younger couples, maybe in their 20’s or early 30’s when men are so much more skittish. But when a man reaches 35 (and you do too) I truly believe that requesting what you want in the relationship is completely fine. You will learn a lot by doing so. You’ll discover if he wants to please you, stay with you, move forward with you or whatever it is you are asking. As i wrote in a previous post, even the topic of marriage is not off limits. Heck i had to bring it up with my husband and no harm done.

I read somewhere (wish I could remember the source) that it is actually the woman’s job to manage the relationship. Why? Because many men just aren’t inclined to move ahead naturally. Status quo is great – why mess it up?

The point is for Melanie and any woman out there in a relationship, if there is something you want to step up in your relationship, might as well bring it up and ask. If the man reacts badly – you have learned something important and can stop wasting time with him. And if he is open to taking the next step – hurray – you don’t need to wait any longer. Not much of a risk in the long run.

Get your needs met. Be reasonable yes. Delivery can be everything so don’t be demanding or stomp your feet. Don’t make the conversation a big deal. Pick your timing and your words well. And then bring up the subject lightly, like  you just thought of it. This is what I said to my husband after 5 weeks of dating and it worked like a charm:

"Paul, I really enjoy our time together. It’s fun seeing you on the weekends. I think it would be fun during the week too." He smiled and thought it was a good idea too. We started to see a lot more of each.

A simple request – a big move forward. Give it a shot.


Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

Leave a Comment