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EVOLVING WOMANHOOD

20 Wedding Regrets I Would Avoid If I Ever Got Married Again

Sep 29
15 min read

Updated: 5 days ago


 

When I got married almost 30 years ago, wedding planning looked very different.

 

We didn't have Pinterest boards full of weddings that looked like small royal events.

 

There weren't wedding content creators following brides around with phones.

 

Nobody was asking me whether I wanted a champagne wall, an audio guest book, a private last dance or three different outfits for one night.

 

And somehow, even without all of that, planning my wedding still stressed me out.

 

I didn't have a big circle of friends helping me make decisions or taking things off my plate.

 

 I didn't have much family around besides my immediate family.

 

My mother was basically the only person helping me, and let's just say she had plenty of opinions about how my wedding should go.

 

Sometimes it felt less like she was helping me plan my wedding and more like I had been hired to coordinate hers.

 

Looking back, I can laugh about some of it.

 

Some of it still wasn't funny.

 

What I remember most is that wedding planning felt like work.

 

There were so many decisions, and when you don't have much support, every tiny choice eventually feels like one more thing somebody needs from you.

 

So, if I ever got married again?

 

I would approach the whole thing very differently.

 

Not because I know how to plan the perfect wedding now.

 

I don't.

 

I just know I would care a lot less about creating a perfect wedding and a lot more about actually enjoying the one I was paying for.

 


1. I Would Decide What I Could Really Afford First

 

This would come first.

 

Before touring the beautiful venue.

 

Before trying on the dress that's mysteriously three times what I planned to spend.

 

Before looking at flowers.

 

Before Pinterest convinces me that my marriage cannot possibly begin without hanging greenery from a ceiling.

 

Weddings are expensive now.

 

The Knot reports that couples married in 2025 spent an average of about $34,200 on their weddings.

 

That doesn't mean we need anywhere close to $34,000 to have a beautiful wedding.

 

It shows how quickly all those individual decisions can add up.

 

I would pick the number first.

 

Then I'd make the wedding fit the number instead of trying to make my bank account fit the wedding.

 

Here are 3 practical ways to make this easier:


  • Set a hard maximum before shopping. Decide the total amount you’re willing to spend, then leave a little room for surprise costs instead of budgeting every last dollar.

  • Break the total into categories. Pick an amount for the venue, food, dress, photography, flowers, music and other priorities before you start booking anything.

  • Choose your top three splurges. Decide what matters most to you, like photography, food or the venue, and spend more there while cutting back on things you care less about.



2. I Would Remember That Help with Strings Attached Isn't Always Help

 

I needed help when I planned my wedding.

 

What I didn't need was somebody taking over.

 

There's a difference.

 

When somebody is helping financially, emotionally or physically, it can get uncomfortable when that help suddenly becomes voting rights.

 

Now I'd decide early what was actually open for discussion and what wasn't.

 

Advice?

 

Sure.

 

Suggestions?

 

Absolutely.

 

Someone else deciding what my wedding has to look like because they helped pay for something?

 

That's where I'd have to draw the line.


Here are 3 practical ways to make this easier:


  • Ask what the help actually means before accepting it. If someone offers money or help, find out whether it comes with expectations about the guest list, venue, dress, ceremony or other decisions.

  • Decide your nonnegotiables early. Pick the few wedding choices that belong to you and your partner, then make that clear before family opinions start piling up.

  • Give people specific ways to help. Instead of handing someone open ended control, ask them to help with one clear task, like researching florists, picking up decorations or handling transportation.


 

3. I Would Accept That Wedding Planning Really Is a Lot of Work

 

I used to think maybe I was doing something wrong because I wasn't having this wonderful time planning everything.

 

Now I know better.

 

There are venues, vendors, contracts, guest lists, seating arrangements, food, music, clothes, transportation, photographs, invitations and approximately 714 other decisions nobody mentions when someone asks, “So when's the wedding?”

 

At some point I would probably tell my future husband, “You pick. I no longer have an opinion about napkins.”

 

And I would mean it.


Here are 3 practical ways to make this easier:


  • Split the planning instead of carrying all of it. Give your partner full responsibility for certain things, like the DJ, transportation, hotel blocks or rehearsal dinner.

  • Make decisions in batches. Pick one night for invitations, another for food, another for music, instead of trying to think about everything every day.

  • Know when a decision is good enough. Not every choice needs hours of comparing. If two options both work, pick one and move on.

 


4. I Would Hire Someone to Manage the Wedding Day if I Could Afford It

 

This doesn't necessarily mean paying someone to plan the entire wedding.

 

I'd want somebody who knows what's supposed to happen and can handle problems without coming to me every five minutes.

 

Where should the florist go?

 

Ask her.

 

The DJ needs something?

 

Ask her.

 

Uncle somebody can't find his table?

 

Please, for the love of everything, ask her.

 

My bridesmaids and family are here to celebrate, not work a shift.


Here are 3 practical ways to make this easier:


  • Hire a day of coordinator instead of a full planner. This can cost less while still giving you someone to handle vendors, timing, setup questions, and little problems on the wedding day.

  • Create one main contact person for vendors. Give the florist, DJ, photographer, caterer, and venue one person to call so they’re not coming to you for every question.

  • Make a wedding day problem list ahead of time. Decide who handles things like missing decorations, late vendors, seating confusion, gifts, and last minute changes before the day starts.

 


5. I Would Be Very Careful About Who I Hired to Take Pictures

 

I would look at more than someone's ten prettiest Instagram pictures.

 

I would ask to see entire weddings.

 

I want to know what the pictures look like indoors, outside, in bad lighting, during the ceremony, on the dance floor and when people aren't posing.

 

There are things from a wedding we can buy again.

 

Photography isn't one of them.

 

Once the day is gone, it's gone.


Here are 3 practical ways to make this easier:


  • Ask to see full wedding galleries. Don’t judge a photographer by a few perfect social media photos. Look at an entire wedding from getting ready through the reception.

  • Check how they shoot different lighting. Make sure you like their indoor photos, nighttime reception shots, outdoor photos, and candid pictures, not just posed portraits.

  • Ask about their backup plan. Find out what happens if their camera fails, they get sick, or something goes wrong with the files. Your wedding photos are too important to leave to chance.

 


6. I Would Tell My Photographer Exactly Who Matters to Me

 

I wouldn't write “family photos” and assume the photographer will know who to take pictures of.

 

I'd make a short list.

 

My parents.

 

My children.

 

Grandparents.

 

Closest friends.

 

Favorite aunt or uncle.

 

Whoever matters to me.

 

Because the photographer doesn't know that the woman standing quietly in the corner has known me since I was ten.

 

Years from now, I don't think I'm going to wish I had seven more photographs of the centerpiece or decorations.

 

I will wish I had one more picture with someone I loved.


Here are 3 practical ways to make this easier:


  • Make a short must have photo list. Write down the names of the people you absolutely want pictures with so nobody important gets missed in the rush.

  • Tell the photographer who the key people are before the wedding. Point out grandparents, close friends, children, or relatives who may not be in the wedding party but matter deeply to you.

  • Ask for candid photos of the people you love too. Don’t only plan posed group shots. Ask the photographer to capture natural moments with the people you’ll want to remember years from now.

 


7. I Wouldn't Spend Half My Wedding Posing

 

Here's where I contradict myself.

 

Yes, I want beautiful pictures.

 

No, I don't want to disappear for two hours posing for them.

 

I want to attend my own wedding.

 

I would plan enough time for good photos and then go eat, dance, laugh and be with the people who came to celebrate with me.

 

There has to be a point where we put the camera down and live in the moment we're trying so hard to document.


Here are 3 practical ways to make this easier:


  • Set a time limit for wedding photos. Decide ahead of time how long you’re willing to spend on formal pictures so photography doesn’t take over the reception.

  • Take some photos before the ceremony. A first look or early wedding party photos can free up more time afterward to actually enjoy your guests.

  • Choose the photos that matter most. Focus on the couple, close family, wedding party, and a few favorite portraits instead of trying to recreate every pose you saved online.

 


8. I Would Make Sure Someone Recorded the Important Parts

 

I don't know that I'd need an expensive movie production.

 

But I would want my vows recorded.

 

The ceremony.

 

Important speeches.

 

Maybe the first dance.

 

There are voices we're convinced we're going to remember exactly forever.

 

Life has taught me otherwise.

 

I'd want those moments somewhere I could hear them again.


Here are 3 practical ways to make this easier:


  • Pick the moments you’d be heartbroken to lose. Decide ahead of time whether you want the vows, ceremony, speeches, first dance, parent dances, or another meaningful moment recorded.

  • Ask one reliable person to handle it. If a videographer isn’t in the budget, choose someone you trust to record the important parts instead of hoping a random guest remembers.

  • Check the setup before the wedding starts. Make sure the phone, camera, sound, storage, and battery are ready so the recording doesn’t cut off halfway through something you can’t redo.

 


9. I Would Actually Sit Down and Eat the Food I Paid For

 

This shouldn't require its own section.

 

Yet here we are.

 

I would eat breakfast.

 

I would have something before the ceremony.

 

And after spending all that money choosing a dinner menu, I would sit down and eat the food.

 

Nobody needs me fainting dramatically beside the cake because all I've had since 8 a.m. is champagne and half a strawberry.


Here are 3 practical ways to make this easier:


  • Put meals into the wedding day schedule. Plan breakfast, a snack before the ceremony, and actual time to sit down for dinner.

  • Have someone bring food to you if needed. Ask a bridesmaid, coordinator, or trusted person to make sure you get a plate instead of getting pulled away all night.

  • Keep easy snacks and water nearby. Protein bars, fruit, crackers, or something light can help if the day gets busy and meals are delayed.

 


10. I Would Wear the Beautiful Shoes and Bring the Comfortable Ones

 

I'd still wear the shoes I loved.

 

For a while.

 

Then those shoes would be coming off before my toes filed for divorce.

 

I would bring comfortable shoes and feel no shame whatsoever about changing into them.

 

Nobody looking at my wedding album 20 years later is going to ask why I wasn't suffering enough.

 

Here are 3 practical ways to make this easier:


  • Break the shoes in before the wedding. Wear them around the house a few times so you know where they rub, pinch, or hurt before the big day.

  • Bring a comfortable backup pair. Keep flats, sneakers, sandals, or low heels nearby so you can change once your feet have had enough.

  • Choose shoes that work with the venue. Think about grass, stairs, cobblestone, dancing, and how long you’ll be standing before choosing the heel height.



11. I Wouldn't DIY Everything Just Because I Could

 

Wedding Pinterest can have us believing we're one hot glue gun away from becoming professional decorators.

 

Sometimes DIY saves money.

 

Sometimes DIY means spending $163 on supplies to make something I could've purchased for $85.

 

I would choose a few things I actually enjoyed making.

 

The rest could be bought, rented or skipped.

 

Because I don’t want to be sitting on the floor at midnight three days before my wedding tying ribbon around 125 tiny jars.

 

At that point, we've gone too far.


Here are 3 practical ways to make this easier:


  • Choose only a few DIY projects that are actually worth it. Pick the ones you enjoy or that save real money, and skip the rest.

  • Price out the full DIY cost first. Add up supplies, tools, printing, shipping, and extra materials before assuming homemade will be cheaper.

  • Set a cutoff date for DIY projects. If it isn’t finished well before the wedding, buy it, rent it, or let it go instead of turning wedding week into craft week.

 


12. I Would Spend Less Money on Things Nobody Will Remember

 

This is where I'd really change.

 

Fancy signs.

 

Elaborate favors.

 

Tiny personalized objects.

 

Overdone table decorations.

 

Little details that take hours to choose and seconds for guests to walk past.

 

I'm not saying I'd have no decorations.

 

I love beautiful things.

 

I'd just ask myself whether I'm buying something because I genuinely love it or because the wedding internet convinced me every empty corner needs decorating.


Here are 3 practical ways to make this easier:


  • Ask whether the item changes the guest experience. If it doesn’t make the day more comfortable, memorable, or enjoyable, think twice before spending money on it.

  • Pick one or two decorative details you truly love. Let those stand out instead of trying to decorate every table, wall, doorway, and corner.

  • Wait before buying trendy wedding extras. Save the idea for a few days, then ask yourself if you still want it or if Pinterest just made it feel necessary.

 


13. I Would Leave Breathing Room in the Schedule

 

I don't want my wedding timeline looking like an airport departure board.

 

Hair.

 

Makeup.

 

Pictures.

 

Ceremony.

 

More pictures.

 

Cocktail hour.

 

Entrance.

 

Dance.

 

Dinner.

 

Speeches.

 

Cake.

 

More dancing.

 

More pictures.

 

Sunset pictures.

 

Outfit change.

 

Girl, when are we using the bathroom?

 

I would leave empty space.

 

Real empty space.

 

Here are 3 practical ways to make this easier:


  • Build extra time between the big moments. Give yourself a little cushion after hair, photos, the ceremony, and dinner so one delay doesn’t throw off the whole day.

  • Choose fewer scheduled activities. You don’t need every tradition, dance, photo idea, and reception moment packed into one night.

  • Protect a few quiet minutes for yourself. Leave time to eat, use the bathroom, breathe, talk to your partner, or just look around without someone telling you where to go next.



14. I Would Spend More Time with the People Who Came

 

This is one I think about differently now that I'm older.

 

Some of the people at our weddings won't always be here.

 

Some relationships will change.

 

Families change.

 

Friendships change.

 

People move away.

 

People get older.

 

If someone I love traveled across the country to watch me get married, I would want to spend time actually talking to them.

 

Not waving from across the room while somebody tells me it's time to cut the cake.


Here are 3 practical ways to make this easier:


  • Choose a few people you want real time with. Make a short list of the family members and friends you don’t want the night to pass without talking to.

  • Create a little guest time on purpose. Leave a pocket of time after dinner or before dancing to walk around, sit with people, hug them, and actually catch up.

  • Cut something from the schedule if you need to. If every tradition is pulling you in another direction, skip one so you have more time with the people you may not get another night like this with.



15. I Would Think About My Guests' Comfort More Than Impressing Them

 

If it's hot, I want water and shade.

 

If it's cold, I want warmth.

 

If people have to walk a long distance, I want to think about older relatives and anyone who may have trouble getting around.

 

If there is a long wait between the ceremony and reception, I'd want people to know where they're supposed to go.

 

Guests probably won't remember the exact shade of my napkins.

 

They absolutely will remember sweating outside for an hour without water.


Here are 3 practical ways to make this easier:


  • Plan for the weather, not just the look. If it’s hot, have water and shade. If it’s cold, think about heaters, blankets, or indoor space.

  • Think about how easy it is for guests to get around. Consider parking, walking distance, stairs, seating, bathrooms, and older relatives who may need a little extra help.

  • Don’t leave guests wondering what happens next. If there’s a long gap between the ceremony and reception, give them clear directions, a place to wait, or something comfortable to do.

 


16. I Would Have a Real Weather Plan

 

Not a hopeful weather plan.

 

A real one.

 

If the wedding is outside, what happens if it rains?

 

If it's extremely hot?

 

Cold?

 

Windy?

 

And most importantly, would I actually be okay with the backup location?

 

“Everybody squeezes under that little covered area” is not a weather plan.

 

That's an emergency.


Here are 3 practical ways to make this easier:


  • Ask to see the backup space before booking. Don’t just accept “we have an indoor option.” Walk through it and make sure you’d still be happy having your wedding there.

  • Plan for more than rain. Think about extreme heat, cold, wind, mud, and strong sun, then decide what guests would need to stay comfortable.

  • Choose a deadline for making the weather call. Decide ahead of time who will make the final decision to move things indoors so you’re not standing in your dress refreshing the weather app every three minutes.

 


17. I Would Give Hair and Makeup More Time Than I Thought We Needed

 

I would build extra time into the morning.

 

Because one person being late can make the next person late, and suddenly the entire day is running behind before I've even put the dress on.

 

I don't want to start my wedding day looking at a clock every six minutes.

 

I already spent enough of my first wedding stressed.

 

I wouldn't volunteer for more.


Here are 3 practical ways to make this easier:


  • Add extra time to the getting ready schedule. If hair and makeup are supposed to take three hours, give yourself more room instead of planning everything down to the minute.

  • Start with the people who take the longest. Ask the hair and makeup team who should go first so one complicated style or makeup look doesn’t hold up everyone else.

  • Set a hard finish time before you need to leave. Aim to have hair and makeup completely done well before the ceremony so you still have time to get dressed, take pictures, eat something, and breathe.

 


18. I Would Assign Someone to Take Care of Everything at the End

 

By the end of the night, I already know my brain would be finished.

 

Who's taking the cards?

 

The gifts?

 

My purse?

 

The leftover cake?

 

Decorations?

 

My shoes?

 

Whatever random item I apparently brought and completely forgot about?

 

I'd decide all of that beforehand.

 

Future me would appreciate it.


Here are 3 practical ways to make this easier:


  • Give specific items to specific people. Decide ahead of time who is taking the cards, gifts, leftover food, decorations, dress items, and anything else home.

  • Use labeled bags or boxes. Have containers ready for things like cards, personal items, decorations, and leftovers so nothing gets mixed up or left behind.

  • Make one person the final checker. Ask someone you trust to do one last walk through before leaving and make sure nothing important is still at the venue.

 


19. I Would Stop Treating Every Little Problem Like a Wedding Emergency

 

Something is probably going to go wrong.

 

Maybe somebody is late.

 

Maybe a flower falls off.

 

Maybe someone cancels.

 

Maybe the DJ plays the wrong song.

 

Maybe Aunt Somebody sits at the wrong table and creates an international incident.

 

I would ask myself one question.

 

Will this actually matter tomorrow?

 

If the answer is no, I would try very hard to leave it alone.

 

Because I know how easy it is to let stress steal the memory we're trying so hard to create.


Here are 3 practical ways to make this easier:


  • Decide what counts as a real emergency ahead of time. A medical issue, missing vendor, or major weather problem needs attention. A crooked centerpiece or wrong song usually doesn’t.

  • Give small problems to someone else. Let your coordinator, bridesmaid, or trusted person handle things like seating mixups, missing decorations, or late deliveries so every issue doesn’t land on you.

  • Use the “will this matter tomorrow?” rule. If the answer is no, let it go and get back to the people, food, music, and moments you actually want to remember.

 


20. I Would Remember Why Everyone Is There

 

This might be the biggest thing I would do differently.

 

I spent so much of my first wedding planning experience worrying about decisions, opinions and everything that had to get done.

 

If I ever had another wedding, I would want moments when nothing needed me.

 

I would sit beside the man I just married.

 

Look around the room.

 

Eat the cake.

 

Watch people dance.

 

Take in the people who showed up.

 

And remind myself that the wedding wasn't successful because every flower was in the right place.

 

It was successful because we got married.

 

That's the part I think we can lose when wedding planning starts becoming another full-time job.

 

There are more wedding choices now than there were when I got married almost 30 years ago.

 

There are probably more options than any of us actually need.

 

But maybe that makes knowing what matters even more important.

 

If I ever planned another wedding, I wouldn't try nearly as hard to make everything perfect.

 

I'd prepare more.

 

I'd ask more questions.

 

I'd protect my budget.

 

I'd accept help without handing over the whole wedding.

 

I'd take the pictures.

 

I'd talk to the people I love.

 

I'd wear the comfortable shoes.

 

And somewhere in the middle of all of it, I would make sure I was actually there.

 

When everything is over, I don't think we'll care nearly as much about what went wrong as we thought we would.

 

We'll remember how it felt to be surrounded by the people we loved.


Here are 3 practical ways to make this easier:


  • Plan one quiet moment together. Step away for five or ten minutes after the ceremony or during the reception and just sit together without pictures, speeches, or anyone needing something.

  • Choose one moment to stop and take it all in. Look around the room, notice who came, watch people laughing and dancing, and let yourself actually feel the day instead of rushing to the next thing.

  • Pick a reminder phrase before the wedding. Something as basic as “we already did the important part” can help when a small problem happens and you feel yourself getting pulled back into stress.


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