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February 14, 2024 22 mins

Transitioning from dating to engagement can pose challenges that can test the foundation of your impending marriage. Trust us, we've been there – Kaylin returned her ring more than once during this topsy-turvy phase of our relationship. In this episode, we share our personal journey and unveil six effective strategies to not only preserve your sanity but also nurture the love that might seem threatened during these tumultuous times.

#RelationshipPodcast #DatingToEngaged #LoveAndSanity

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
(00:00):
Going from dating to engage can absolutely ruin your upcoming marriage.
I gave my ring back twice, maybe three times. Maybe three times.
So we're going to talk through six big pitfalls to make sure you're a void when
you go from dating to engage, coming up.
Our engagement wasn't exactly frogging through a field of dandelions and roses

(00:21):
or flowers, whatever kind of flowers you want to put in that field.
The engagement itself was awful. No, no, no. It was terrible.
The proposal was awesome.
That was awesome. We'll save that for another episode.
The engagement season. The season of engagement. Is probably.
It's so weighty. There's so much. It's like being locked in a dungeon.

(00:46):
Stuck with someone. You're like, I'm going to be stuck with this person the rest of my life? Gosh.
I can't wait. It's so exciting. There's just a lot of stress and pressure.
And lots of emotions in between.
It's the upside down, the upside down. Yes. Engagement is like the upside down
of a relationship. Yeah. Nothing.

(01:08):
Everything's sort of familiar, but nothing is quite as it seems.
And it's all sort of dark, gloomy, scary and terrifying.
There are some good moments. There are some great moments. So we're going to
talk through today some of the biggest pitfalls, things to avoid,
things to make sure you do when you go from dating to being engaged.
Because I think that we learned a lot during our engagement personally.

(01:31):
Yes. And I think some of this advice is like things we wish we did and maybe didn't do.
Failed at miserably. Exactly. So maybe you can do better than us.
So we have six tips, six pitfalls to avoid, if you will. But before we kind
of get into that, I do want to talk through what I think is the number one biggest
pitfall. And I thought this was really interesting.

(01:52):
I was doing research before we started this show. Of course you were. As I like to do.
One of the most interesting things that I found when I was digging through the
books, doing some research, was that today, in the modern age,
70% of couples live together before they get married.
70%, which I found to be astronomical. Now, the crazy part of it— Is it surprising? Surprising.

(02:13):
I thought it was, I was a little surprised about it because I mean,
I get that people, times are tough.
Finances can be hard. It's a lot easier to move in with your spouse.
And maybe, and this is, you know, maybe for another time, another show,
it was maybe because I did live with a girlfriend prior to getting engaged. And that was awful.
I learned so much through that experience. Who did you live with before we got

(02:35):
engaged? Not important.
Back to of the facts, of that 70%, when they got married, they had a 48% higher
chance of getting divorced five years later down the line.
Not one of our official six pitfalls from dating to engage, but something to
consider and think about. I mean, obviously, that's a huge one.
You're getting engaged.

(02:55):
You're hoping to build a life together. You want to make sure it's going to
last and be sustainable. So maybe don't live with your boyfriend or girlfriend before then.
Yeah. I mean, I'm not surprised by that one.
I also am a kid of divorce.
So the rate of like me getting a divorce is already higher. She's like at 100%
if she were to live with someone beforehand. Oh, definitely don't do that.

(03:19):
All right, let's dive in. Number one, don't let the list get you pissed.
What do you love? This is my favorite one. I worked on that for about two seconds.
But what I mean by this is there is a long list of to-dos when you go from dating to engaged.
During the dating period, you're not worried about bank accounts.

(03:40):
You're not worried about cell phones. You're not worried about living together.
You're worried about just spending time together.
When you get engaged, you got to worry about all that stuff.
Plus, most likely a wedding to plan or an elopement to plan.
End, no matter what you're going to be planning, there is a lot to get done
in what can sometimes be a short amount of time. Plus a honeymoon.

(04:00):
Plus a honeymoon. Let's not forget about that. And so there's this long list.
Don't let it get you pissed.
And I think in order to do that is you really got to focus on not what has to
be done, but what needs to be done.
So what actually has to be accomplished before we say, I do, we walk down the aisle.
I know a big thing for us, and this is controversial, and it was controversial
even between us, was we didn't necessarily figure out our living situation until after the wedding.

(04:29):
And there was pros and there was cons to that.
Pros was that we weren't worried about it at all. Cons was that we weren't living
together when we first got married.
We're like, well, what home are we going home to? I don't know.
We'll figure it out. We were living together.
It just was like, we're living at your place and And we're living at my place.
But you don't have a drawer.

(04:49):
And I don't have a drawer. It's like living with each other with a day bag. Exactly.
But at the same time, it all worked out. Stuff done.
We got the important stuff done. And there was honestly so much going on.
And we were potentially looking at relocation with my job at the time,
which ended up happening. So it was good that we didn't really figure it all out.
Because if we would have found a place to live in, that would have been tied up with a lease.

(05:14):
So so it all worked out and we're very
blessed how it all came together at the end of the day but find those
things for you i mean for us it was we kind of put the living
situation on the back burner uh everyone's going to have something
they could put on the back burner and and take advantage of that you know don't
don't feel the need to get everything done because you're going to just have

(05:35):
an awful engagement period this is coming from a type a personality who likes
to get everything done yeah well i think one of the reasons this is all this
is one of my top don'ts is because I was so type A about it,
I think especially at the beginning. I was like, we got to figure out everything.
And as we got closer to the wedding. I had to ride because of it, like always.
There was lots of tears. But as we got closer to the wedding,
I started to let go of more and more things.

(05:57):
It's okay if we don't get this done. Yeah, it was good for my mental health.
I think it was good for our relationship.
Probably, yeah. So don't be like me. Don't let that list get you pissed.
Okay, my turn. Your turn. Mine is not as clever, but don't delay merging your
lives. And I mean this like mentally.
Start having conversations about bank accounts and different things like that.

(06:19):
It doesn't need to get done, but if you haven't had those conversations in your
dating relationship, it's time to mentally.
Yes, wedding planning is probably the most important priority on your list,
but start having conversations.
Who's going to manage the bills? Where do our strengths play to our relationship
so that when marriage does come, you are mentally prepared for it?

(06:42):
For us, we did not get everything done on our list.
We didn't figure out where we were living, but we did want to find a church
together that we both liked, that we started anew at, that knew us as the Raps
and not Caitlin and Justin.
Because at the time, I was going to a church that I grew up in,
so it was good that we had something that was our own. You're creating that

(07:05):
joint identity as opposed to those individual identities.
Yes. And that's really important during this phase. It is. It's very important
because that's what marriage is all about.
And having those big conversations is super important. And because we found
this church, we started doing premarital counseling and having all those big conversations.
Little did I know, Justin had sneakily put all these conversations into our dating relationship.

(07:27):
So we had already aligned on so many things before before we got married.
But at the same time, like everyone's different. You could be 22 getting married.
You could be, you know, in your forties, previously divorced with kids.
There's conversations you need to have before you get married.
I think one of the interesting things about premarital for us is that,

(07:49):
you know, we kind of became the teacher's pet because I've always been teacher's pet.
So has Caitlin. So, you know, it was inevitable, but I mean,
truly they were saying like wow you guys have talked through so much of this
like a lot of the people we have across from us on this couch or you know as
Kayla just mentioned their kids in their 20s for the very first time and so
I think for us and I think you'd agree was that you know us having so many of

(08:11):
those conversations before,
premarital was a huge bonus I mean it was so helpful and so just a little a
little side tip for all my guys out there listen.
You know, when you're dating, it's going to come, it's going to hit the cliff at some point.
You know, I've been there, like the six pack fades away and the charms will fade away.

(08:32):
And so, and as you're dating, you know, you want to be intentional about those
conversations you're having with, you know, your possible future partner.
And one of the things that I was very intentional about, and Caitlin will attest
to, is that we had a lot of these conversations even before engagement was on the table.
And so, you know, even if you're out there just dating right right
now it's never too early well i mean there is a don't do

(08:54):
a date one guys but like but you're dating with intention if
you're dating with intention have this conversation okay sidebar though
we on our first date you were like what do you want to do with your life and
i was like i want to be a mom and most people would be freaked out and he was
like okay it's like great check that sounds great because i want kids so i mean
but no know what you want and this is a whole other conversation on like knowing
what you want when you date but having gone through the gauntlet of women that

(09:17):
I went through, I knew what I did not want.
I had a long dating history. It's like a Thanos gauntlet.
But knowing what you want to be and intentional and having those intentional
conversations, I think it's just so important as Caitlin was talking about.
Exactly. So don't delay merging your lives mentally.

(09:37):
All right. This is a big one. Don't underestimate that you are joining a new
family. family. You're starting a new family too.
Yes, it's both. It's like you're starting your new family, but it's linking
onto a chain of your family and my family and all that.
But the old saying goes, you're not just marrying the girl, you're marrying

(09:59):
her mom. And you're also marrying his mom.
My mom's a sweetheart. Not that your mom isn't, but they all are great.
But you really are are marrying into this new family.
And so I think one of the things for me that didn't become really obvious or
apparent until we were like,
getting close to the wedding. Cause as you get close to the wedding,

(10:20):
everything heats up, people have more opinions, everyone's got more emotions.
So I started to realize like, wow, I like, I'm, I'm going to be a part of this family.
When, who's, who, where are you spending Christmas?
Yeah. The holiday questions start coming up and all that good stuff.
So don't delay trying to be part of this family.

(10:40):
Once you all are engaged, you know, we were talking about before recording here.
And I was saying that, you know,
in a way, I kind of feel like at an arm's distance from your parents.
And Caitlin shared with me, that's kind of how her parents are with people until
they're like in the family.
You're not in the fold until you're like in the fold. And let me tell you,
once I was in the fold, I was in the fold.
Like I felt like I was in it. And that arm was instantly removed.

(11:03):
And so I think it was a kind of a shock for me because I think one of the things
I learned and if I could do it over again was don't delay being that that brother-in-law
or that sister-in-law or that son-in-law, you know, right off the bat,
it's, it's kind of a new role because it is, it is you, you're functioning in
a family in a completely way, new way that you never have done before.

(11:23):
And totally changes the dynamic of like your family too, like with this new person.
Right. Bringing, bringing, making sure you're making your, your,
uh, your significant other or part of, of your family.
There's just, there's just so much that goes into it of just merging families together.
And, you know, know we were very lucky that our families get along really
well and even though they they didn't really they hadn't

(11:45):
met until the wedding weekend really they met once during our engagement but
that was pretty short and so but things went swimmingly and i was kind of nervous
i know caitlin probably was too because our families are very different but
it all worked out so everyone was on their best everyone was well behaved we gave you know.
Pep talks to both of our respective families. So no, but it's just,

(12:10):
you are joining a new family. You're creating your own new family unit.
You're joining another family, established family unit.
You're bringing your significant other into a family unit. So there's just a
lot of new blood circulating in these family conversations and these dynamics.
So just don't underestimate that.
And it's okay for it to kind of be overwhelming and emotional at times.

(12:30):
You're going to get through it. The biggest thing is make sure that this is your number one.
I know one of the things that I told my parents, and everyone is different,
but one of the things I told my mom and dad straight up was like,
listen, if you've got a problem with Kaylin, you come to me.
And I just know how my parents can be sometimes.
And so that was really important that I kind of had control,
a kind of a dam, if you will, to make sure that I kept all the healthy boundaries.

(12:55):
Exactly. So you have those conversations with your parents.
Don't be afraid of those conversations, have this conversation with your significant
other, your spouse, really important as you go through this phase.
So just don't underestimate the big change that it can be though. Yeah.
Also, next point would be don't go crazy, like lose your mind and be committed

(13:15):
and put into a straitjacket crazy like I almost did.
Wedding planning is stressful. Committing to a person for your entire life is
a daunting fear for some people.
It can bring up a lot of insecurities. For me, it brought up insecurities from
my childhood. It brought up insecurities I didn't even know I had.
Just make sure you have clear communication with your partner.

(13:37):
Make sure you're discussing things.
If you are freaking out, go to them. Tell them why. If you can't put it into
words and they can't put it into words for you, maybe you need to seek professional
help. There's no shame in that. I wish I did it.
For us, for me, I know when we We were engaged.
I was watching one of my best friends' marriage fall apart, not by her own effort

(14:00):
or just diligence as a lovely human being, but just she had a bad partner who changed his mind.
And I let that fear and insecurity enter into our relationship.
And I was projecting things on Justin that were not fair and not true.
So, you know, that's when she gave the rings back a few times.

(14:23):
You deserve one of them one of them maybe responsible for one but but like i
also have divorce pains and fearful of you know someone leaving me so i think
i wanted to give my ring back before they could take it away i don't know so just make sure you.

(14:43):
Are aware of what's going on, have clear communication with your partner and
your partner can be like, Justin is so good at like, what's going on?
Let talk to me. Is this what's going on? Like he can figure me out before I
can figure me out sometimes.
Well, we often can, right? Having that outside perspective is so helpful.

(15:05):
And so your partner should really be there for that and really dive into it
and really try to figure out well, what's going on?
I mean, you know, you spoke about the divorce coming from divorced parents and stuff.
I remember one time we were having a conversation and I'm going to butcher it.
It's not an exact quote, but you know, you said something along the lines of
basically like, hey, I'm scared to get married because if I love you and then

(15:26):
you leave me, it's going to hurt so much more.
You know, not in that exact way, but that's basically what we got to one evening.
And, you know, it's just understanding those fears of your partner.
And just, it's such an emotional time.
Everyone's got high emotions. And just taking time to talk and understand each
other and figure out where each other are coming from is,
I think, just such an important thing to do, not only during this period,

(15:50):
but just in your relationship in general.
Whether you're dating, whether you're engaged, or whether you're married,
you got to be there for your partner. This is your number one.
If you can't rely on that other person, then maybe you're not in the right relationship,
truly. Truly, truly, truly.
Next one. next one next number five should
have been doing a countdown for all of them don't stop dating

(16:13):
it seems stupid it seems simple
you can sink throughout it it's great i like it you know but it's
it's just don't stop doing it you know
i stopped doing this well i was
just about to say i think that for myself this
is something i was not very good at i'm a very type a
personality personality i got a list i got a list of lists i

(16:34):
got an inception of lists going on and so when it came to joining
our lives together from the wedding planning to merging
our lives i mean there was lists about everything and so i could very much on
a friday get together we're getting dinner and be like cool what are we going
to accomplish like what are we going to get done this week and what's let's
go through the to-do list of things we're going to we're going to knock out
let's talk about table arrangements let's talk about flowers talk about this

(16:57):
stuff and you know and i want to be You wouldn't love him.
Yeah, and I wasn't loving on Kaylin the way I probably should have.
And so I think one of the big realizations that we had was that we just need
to make sure that we continue to keep dating.
And I think it was, you know, a couple months into the engagement period where
we realized this and just taking that time.
It doesn't have to be a lot. It doesn't have to be like every weekend's a big

(17:19):
date. But like we would go to our favorite restaurant.
Our favorite bartender, Peter, would be there. And we just have dinner.
And that dinner would be, we're going to focus on nothing, nothing wedding related,
nothing married related. We're
just going to have a conversation like we used to when we were dating.
And that really helped us keep our sanity throughout.
So don't underestimate the power and just having a dinner like that every once

(17:40):
in a while to keep the sanity going. Yes. Love that.
All right. That brings us to our very last one. Don't die on every hill. Choose your battles.
Wedding planning is stressful. Lots of emotions, lots of family involved.
Lots of opinions. Lots of opinions. Talk to your partner, ask them what's most

(18:01):
important to them, and focus on those things.
And then delegate those other items that maybe are not a huge priority for you
both, but play to your family's strengths.
So get your family involved in wedding If they want to be for me,
my mom wanted to be involved.
Our thing was photography, videography, music.
We focused on that. My mom was great at decor and flowers. We delegated that.

(18:26):
It was beautiful. She did an incredible job.
We got to have our photos and videos the way we wanted. The music set the tone for the wedding.
It just, it worked out for us to delegate those things, made her feel special and involved.
It turned out. I think that's the big thing, right?
We are so blessed. Let me just start by saying that.

(18:48):
We are so blessed that one, Kaylin's parents had money aside to help pay for a beautiful wedding.
And then number two, that our parents wanted to be involved.
I know a lot of people get married, they don't have any financial help.
Their parents don't want to be involved in it.
It's sad. Honestly, that's when you got to rely upon your friends.
You got to rely upon that circle around you. You got to rely upon your church,

(19:10):
whatever it might be around you.
So let me just start by saying we were so blessed that everyone wanted to be
involved to the point where it was almost like, I don't know what you can do.
But I think we got it covered. Yeah. Kaylin just nailed it so perfectly.
Like we had a lot of opinion. Well, I had a lot of opinions and a vision for

(19:31):
the wedding. Lots of visions. Probably more so than Kaylin even did.
I didn't care as much. I just wanted to be pretty and the food to taste good.
So the fact that she was dealing with her husband actually being the opinionated
bridezilla, which is kind of funny.
We had a vision and we kind of had laid out the vision. And once we had the
vision, we kind of wanted to execute the vision.

(19:52):
And then we were finding ways to get people involved where they could run with their vision.
Your mom had a vision for the wedding. It wasn't always exactly what we had
vision. but then she did things like the table setting and it was gorgeous and
the flowers and it was perfect.
And it was great. And she ran with it. And I think the most important thing
about it is as Kaylee laid out, her mom felt involved and a part of the process.

(20:15):
And so anyone who wants to be involved in your wedding, try to find a way to get them involved.
One, it's just, it's, yes, it's your day but it's also like it's everyone's day.
This room filled with people who love you love you
and are so happy for you it's like
the best day yeah and so when you can get them all

(20:35):
involved it's it's fantastic and it also gets things
off of your plate which is super helpful because i think by the as the wedding
got closer and closer we're like take the flowers take the settings like we
got we got so many other things to worry about yeah yeah no i love that so picking
and choosing your battles and not dying on the small hills yeah,

(20:57):
Some things aren't important. Some things are, but some things are not.
The most important thing is this. You keep this real.
You keep, you know, dating, you keep loving each other. You keep assessing your,
your relationship, keep communicating.
That's the big thing. Don't stop talking to one another and you're going to be fine.
And so, you know, this is just some things that we learned from our engagement period.

(21:18):
We had a pretty short engagement. It was kind of fast and furious about eight,
eight months or so, eight months.
So, You know, it was a fun but hectic time.
And so we hope that this helps you as you're getting ready to possibly go on
that adventure, saddle up your horses.
Couldn't help yourself. It's going to be a good ride. Anything else?

(21:39):
You got anything else? That's it.
That's all you got? I think so. All right. Well, hope you liked it.
If you like the show, subscribe.
Click the bell here on YouTube. Leave us a comment. Those are always great.
Those really help us out quite a bit.
If you're listening on wherever you listen to your podcast right now,
you can make sure you follow the show.
You can leave us a review again we appreciate it that's very helpful and you
can follow us on the socials on instagram and the tickety-tock-tock-tock with

(22:03):
nothing else to say i'm justin i'm kaylin catch you later.
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