Dating after 50 comes with a whole new set of questions and sometimes it’s nearly impossible to tell the difference between trusting your gut and letting your anxiety take over.
This week, I’m joined by relationship coach and Love at Any Age host (plus Menopause Love Lounge Host) Laurie Gerber to tackle three VERY real midlife dating dilemmas.
What happens when the good morning texts suddenly stop and he says he’s just “busy”? What if his ex-wife is still calling and texting him years after their divorce? And what do you do when you’ve been exclusive for months, act like a couple, but he still refuses to put a label on the relationship?
Laurie brings the 30 years married and relationship-coach perspective. I bring the perspective of someone who has actually been out here dating after divorce. And while we definitely agree on some things, we don’t see everything the same way.
We’re talking breadcrumbing, communication, sex and attachment, staying friends with an ex, relationship labels, commitment after divorce, and one of the hardest questions of all: When are you being patient… and when are you settling?
If you’ve ever stared at your phone wondering what the hell his behavior actually means, this episode is for you.
⏱️ TIMESTAMPS
00:00 Is he busy… or is he pulling away?
02:43 Dilemma #1: He’s still texting, but something feels off
04:40 Did intimacy change the relationship?
06:30 When does “busy” become an excuse?
08:54 Are you giving him space or playing games?
09:54 The conversations you should have by date three
11:10 The problem with good morning texts
13:18 Andrea’s controversial take: Are good morning texts breadcrumbing?
14:52 Stop guessing and start asking what he wants
16:39 Dilemma #2: His ex-wife is ALWAYS around
18:54 When being friends with an ex is actually okay
20:18 Should you meet his ex?
20:33 Andrea’s relationship with her ex-husband
22:18 When an ex starts marking her territory
23:15 Friendship or emotional dependency?
23:42 How to talk about jealousy without sounding controlling
25:47 Dilemma #3: He wants forever… but not the label
27:44 Why relationship labels actually matter
28:31 When one person wants commitment and the other feels pressured
29:12 When it may be time to step away
29:58 “Consequences are very clarifying”
31:43 Why months 7–8 can reveal real compatibility
32:16 “I need time” vs. being strung along
34:05 Does marriage still matter after 50?
35:19 Patience vs. settling: How do you know the difference?
36:14 Final takeaways
37:17 Send us your dating dilemma
💡 I WANT TO HEAR FROM YOU: If one of these dilemmas hit a little too close to home, I want to hear yours.
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Wondering if you’re even ready to date? Take Laurie’s 5-min quiz to learn your obstacles:
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