When Dating After 40 Leaves You Lonely In A New Relationship

14
Feb

Laura was getting ready for a dinner party where her friend said there would be “some interesting single people.” She wanted to go. She wanted to meet someone.

But standing in front of her closet, she felt her chest tighten. The last time she’d done this—really tried to meet someone—she’d ended up in a relationship that lasted two years longer than it should have. She’d ignored things that bothered her. Made excuses. Tried to be what he needed instead of paying attention to what she needed.

She’d told herself she wouldn’t do that again. But standing here now, she wondered if she’d recognize it happening. If she’d catch herself in time.

She picked up her phone and called Beth.

“I’m nervous about tonight,” she said when Beth answered.

“You’ll be great,” Beth said. “Just be yourself. Have fun with it.”

Laura paused. “I’m worried I’ll meet someone and do the same thing I did before. Just… try too hard to make it work.”

“You won’t,” Beth said. “You know better now. You’ve learned from it.”

Laura nodded, even though Beth couldn’t see her. Because what else could she say? That knowing what she did wrong last time didn’t mean she trusted herself not to do it again?

“Yeah,” she said. “OK.”

She hung up and finished getting dressed.

She kept the conversation easy. That’s the habit she’s afraid of.

Laura could have said more to Beth. She could have explained what still worried her. She didn’t. The conversation ended there.

In her last relationship, she ignored things that bothered her and made excuses when something felt off. Now she’s starting to date again without knowing how she’ll handle those moments when they come up.

Beth offered reassurance, but she didn’t ask what Laura was actually worried about. Laura could have pushed back. She could have said the reassurance didn’t address her fear. But that would have made Beth uncomfortable. So Laura accepted reassurance she didn’t find reassuring and ended the call.

She just did with Beth what she’s afraid of doing on dates. She prioritized keeping things comfortable over saying what was on her mind.

How Feeling Lonely in a New Relationship Begins

Early dates often stay on neutral ground—work, travel, families, routines. When a man interrupts her mid-story and shifts the focus to himself, she may feel irritation. She may even consider saying, “I wasn’t finished.” She decides not to. The conversation continues. The moment passes.

Letting it pass works in the short term. The evening stays easy. There’s no pause where she has to explain herself. Saying something would make things more complicated before she knows where it’s going. So she lets it go.

What makes this confusing is that sometimes letting things go IS the right choice. Not every irritation deserves a conversation. Not every disappointment requires discussion. The question is whether you’re making a considered decision or avoiding discomfort. Are you choosing your battles? Or are you choosing not to have battles at all? In the moment, it can be hard to tell the difference. Both may feel like maturity.

His interruption matters less than what follows it. Laura’s concern isn’t a single moment. It’s the way she tends to respond across many moments, especially early on, when everything is still new.

She accepts plans that leave her tired because she wants to appear flexible. When he’s dismissive about something she mentions caring about, she lets it go—it’s early, she doesn’t want to seem difficult. He cancels at the last minute, and she says it’s fine when it’s not. She handles disappointment privately and acts the next day as if nothing happened.

Each choice seems reasonable by itself. But make these choices repeatedly and they build on each other.

Over time, he learns which topics she lets drop, which requests she says yes to, what requires effort and what doesn’t. Laura ends up in a relationship where the things that bother her don’t come out — and eventually don’t get considered.

The things that bothered her at the beginning still bother her months later. He still does them. She’s said little. Now she’s more invested.

She’s with someone while consistently keeping quiet about the parts of herself that might cause friction. She ends up with companionship but feels alone.

Some men will notice the gaps. Some won’t. But if nothing is said, the relationship moves forward as if everything is fine.

What Happens at the Party

That is the risk Laura sees standing in front of her closet. Her fear isn’t about meeting the wrong men. It’s about meeting someone she likes and then doing what she did before.

She goes to the party.

Forty minutes in, she’s talking to a man who makes her laugh. He’s attractive, quick, pays attention. He asks if she wants to have dinner sometime.

“I’d like that,” she says.

“How about Thursday?”

On Thursday, she has her writing workshop. She’s been going for six months. It’s the one thing she does every week that’s just for her.

She looks at him.

What does she say?

What You Miss

When you avoid tension, you don’t see how he deals with it.

How does he respond when you disagree? What happens when you’re disappointed? Can he adapt when you want something different?

If you’re always adjusting, you only see one version of him.

You’re deciding whether to invest more, whether this could work. But you’re deciding based on how he is when everything goes smoothly. That’s a limited view.

Knowing what went wrong last time doesn’t stop you from doing it again.

That’s where an experienced outside perspective helps. Contact me here.


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