Call Her Daddy: "How To Talk About Getting Engaged"

Host: Alex Cooper
Date: August 24, 2025

Overview

In this episode, Alex Cooper tackles a topic that’s often fraught with anxiety, anticipation, and awkwardness: how to bring up engagement within a serious relationship. Inspired by a caller who was unsure how to discuss getting engaged with her boyfriend, Alex unpacks the cultural myths, communication pitfalls, and empowerment dynamics surrounding engagement talks. She blends her hallmark direct advice, personal anecdotes, and the Daddy Gang’s real-life questions to give listeners the confidence and practical tools to own this conversation.

Key Discussion Points & Insights

1. Why Engagement Conversations Are So Hard ([11:22])

• Rom-Com Myths vs. Reality:
  Alex explains how pop culture romanticizes the surprise proposal, showing women sobbing with joy but glossing over the necessary couple’s discussions that should predate the engagement.

  • "But what you think about in a lot of these movies is like, they literally never show the conversation that hopefully happened prior…what they have mutually agreed upon would be a good timeline for the life that they want to build together." ([13:07])

• Normalizing Honest Conversations:
  Despite the desire for a surprise proposal, Alex insists it’s healthy and essential for couples to be able to speak openly about money, life plans, timelines, and expectations before getting engaged.

  • "An engagement…the physical act, fine, he can have the surprise. But the actual decision that you're getting engaged needs to be a 50/50 decision." ([14:11])

2. Owning Your Power: Why Engagement Is a Joint Decision ([16:40])

• Disempowerment Trap:
  Alex warns against waiting passively for him to propose, urging women to take action and accountability. She points out that relinquishing your place in this major life decision sets an unhealthy precedent.

  • "Why are we giving men so much power when it comes to this giant milestone in both of your lives?" ([16:52])
  • "If you just roll over and give him all the power on one of the first major life decisions as a couple…he will make [future decisions], and then you'll just, like, fall in line." ([17:25])

• If You Can’t Talk… Maybe It's Not the Right Relationship:
  Fear or discomfort about discussing the future is a red flag. If the idea of talking timelines honestly feels scary, consider reevaluating the partnership.

  • "Why would you want to marry someone who you don't feel safe talking to about something that should be so exciting and fun, but more importantly, is one of the biggest decisions that you are ever going to make in your life?" ([18:07])

3. How to Actually Have the Talk ([19:20])

Script suggestion for starting the conversation:
"Hey, babe, I know that we have talked lightly about our future and the more and more serious that we've gotten. I know, you know, like, I love you so much, and I'm in this. And so I wanted to have an open and honest conversation with you about how you're feeling about the natural next steps that come in a relationship, which would be engagement, marriage, do we want kids? Like, how we're feeling about all of that." ([19:45])

• Expect Some Misalignment:
  It’s normal if your ideal engagement timelines don’t exactly match up. Major priorities like career, self-growth, or finances can legitimately affect readiness.

• Critical Pre-Engagement Questions:

  • Do you both want kids?

  • What are your family and religious values?

  • Are you clear on each other's financial situations?

  • Would one of you move for the other's career?

  • "You need to know how much your partner makes before you are marrying them, Daddy gang." ([22:33])

4. Red Flags and Boundaries When He Won’t Talk ([25:01])

• Dismissive Responses:
  If your partner consistently pushes the conversation off (“Yeah, we’ll figure it out”), that’s not acceptable.

  • "First of all, if someone says that to you…Daddy Gang, I’m not going to gaslight you today. That’s not a real answer." ([26:18])

• Don’t Settle for Vagueness:
  Assert your need for clarity and set a boundary: you deserve to know where you both stand—even if the answer isn’t what you want to hear.

  • "Do not let him dismiss the topic. You need to leave the conversation with some clarity on where you both stand on things." ([27:14])

5. What To Do If There’s Been Talk—But No Ring (1 Year, 2 Years… Still Waiting) ([29:08])

• It’s Okay to Check Back In:
  After a year or two since “the talk,” it’s reasonable to revisit the topic honestly, but without aggression.

  • "You’re kind of more checking in, less about the engagement. And I think it’s more of, like, are we still on the same page?" ([30:20])

• Don’t Let Anxiety Build in Silence:
  You shouldn’t be left with a pit in your stomach after going to friends’ engagements, unsure about your own future.

  • "You should never be sitting in your bathroom at night with a pit in your stomach before you get into bed with him, because you guys just attended your friend’s engagement… and you have zero clarity on when yours is gonna be." ([31:15])

6. Self-Awareness: Are You Letting Him Be Honest? ([34:59])

• Ask Yourself:
  Are you creating a space where he could actually tell you if he’s changed his mind? Or are you so focused on getting the ring you can’t see his hesitation?

  • "Are you making it impossible for him to even say that he’s changed his mind? Are you the only one at dinner really talking about your future, and he’s kind of this passive listener?" ([35:38])

• If Something Feels Off—Trust Your Gut:
  Open the conversation, even if it’s just for clarity. Remember, you don’t want an engagement where you have no idea where your partner stands.

7. Personal Reflections—Why Alex & Matt Worked ([39:31])

• Hard Conversations Are Foundation:
  Alex shares that her own engagement/marriage was preceded by many hard, sometimes multi-day conversations about money, family, religion, and values.

  • "We both made a concerted effort to…have some of the most uncomfortable, hard conversations before we even got engaged." ([40:39])

• If You Can’t Communicate, You Aren’t Ready:
  If you can’t even have this talk, you’re not ready for marriage.

  • "If you can't have a hard conversation with your partner about actually something that's really exciting for the two of you, then you probably know that you and your partner [are] on very different pages." ([41:27])

8. Final Message: Take Initiative & Value Your Autonomy ([43:52])

• Ask. Demand Clarity:
  Don’t just wonder—actually talk to your partner.

  • "Stop asking yourself why and just go ask your partner. Mirror, just literally turn to your right in bed and be like, hey, what’s going on?" ([44:07])

• Surprise the Proposal, Not the Decision:
  It's valid to want the proposal moment to be a surprise, but don't abdicate your agency in the decision to marry.

  • "No one person in the relationship should get to call all the shots about what your future looks like…You also deserve to have a say in the decision before a man gets down on one fucking knee." ([45:33])

Notable Quotes and Memorable Moments

• On Hollywood’s failure:
  "Hollywood is like, oh, cut that out. But in a normal, real world, healthy relationship, Daddy Gang, these are the type of conversations that happen and need to happen before a proposal and before an engagement." ([12:42])

• On waiting passively:
  "If you find yourself waiting around, wondering if he wants to marry you… it’s time to take some accountability and take some action and ask this person and talk to this person." ([15:55])

• On setting boundaries:
  "Do not let him dismiss the topic. You need to leave the conversation with some clarity on where you both stand on things." ([27:09])

• Advice for checking in:
  "I just wanted to have a check in with our relationship. I know that two years ago we talked about an engagement… I'm coming to you more as a check in to make sure that we are both on the same page." ([30:01])

• On the proposal not being the surprise:
  "It is so valid to want a proposal to happen and want to be surprised and want to give yourself, like, this gorgeous moment. But also give yourself the autonomy in the decision ahead of time. Like, don't be shocked that you're getting married." ([44:52])

Time-Stamped Segment Guide

• [11:22] – Why we’re anxious to talk about engagement and why it NEEDS to be a conversation
• [16:52] – Why “waiting” for him to propose is a power play and not good for your relationship
• [19:45] – Practical script to open the engagement conversation
• [22:33] – Critical questions couples MUST answer before engagement
• [25:01] – Red flags when your partner avoids the talk
• [29:08] – What to do when you’re stuck waiting after the engagement talk
• [35:38] – Self-awareness: Make space for his truth too
• [39:31] – Alex’s own pre-engagement experience with hard talks
• [44:07] – Stop wondering—just ask
• [45:33] – The proposal as a surprise: What matters vs. what doesn’t

Listener Q&A (Selected Highlights)

Note: Q&A starts ~[47:10]
Alex answers written-in questions on relationships, communication, sexual confidence, and friendships. The tone here is sharp, funny, and caring—classic Cooper.

• How do I ask my boyfriend to clean up without sounding naggy?
  (You shouldn’t have to nag—a clean space is basic respect and adulthood. Have the conversation directly and set expectations.)

• I can’t bring myself to actually date the nice guy I’m seeing, even though he wants more.
  ("This is called settling…Don’t just stay with someone because they’re nice to you. We are literally licking crumbs off the floor, girls.")

• None of my college friends have come to visit my baby. Should I feel hurt?
  (You’re in different life stages and that’s tough. Express your feelings, but don’t rely on them for all your support—seek new friendships with people in your current place in life.)

• I changed my look drastically and now my boyfriend isn’t attracted to me—should I change back?
  (Communicate about the change; don’t hide your feelings, but don’t bend yourself out of shape for his preferences.)

• My partner avoids sex at bedtime—should I be worried?
  ("This man is literally running into the bathroom, locking the doors, and then turning off the lights in the bedroom where you're sleeping…this is not a mistake. This man knows exactly what he’s doing.")

• How do I be more open about sex?
  (Start with reading “smut” books and journaling fantasies to ease shame and build confidence.)

Episode Tone & Takeaway

Alex brings her signature humor, candor, and big-sister energy to a topic that’s often loaded with emotion. She’s blunt about the importance of self-advocacy, clear communication, and not letting social scripts dictate your happiness. Listeners are left with practical words, real scripts, prompts for self-reflection, and a bigger permission slip to take up space and co-create their futures.

“You deserve to have a say in the decision before a man gets down on one fucking knee.” ([45:33])

Recommended For:
Anyone contemplating engagement, feeling uncertain about relationship pacing, or wanting a reality check (and a confidence boost) on how to communicate with their partner.

Daddy gang: if you want to own your future (and not just your engagement story), this episode is a must!