Unique Wedding Challenges for Second Timers

Anyone who says that wedding planning is easy has not had to do it twice.

Sure, you have more experience and have learned a lot from the first time around. You know how early to send the invitations, what to do if the centerpieces arrive a different color than you ordered, and how to create a list of tasks your mother can handle (especially if you need to keep her busy!).

But even if your big day went smoothly the first time (which, let’s be honest, is not always the case), there are added expectations and pressures associated with a second wedding. A lot of emotions from your first wedding and your first marriage may resurface, even if you have been divorced for a long time.

Know that throughout these challenges, you are not alone. Over 12% of men and women have married twice. A second marriage gives you the amazing opportunity to start fresh and go into a lifelong commitment having gained previous experience and learned important lessons. Just like your first wedding day, know that this day is extremely special, and marks the start to an exciting journey full of love.

Below I’ll share the most common challenges that second timers face while planning their weddings, and how to overcome them. Let the planning begin!

The Idea of “Failure”

Challenge: The dissolution of your first marriage was likely surrounded by feelings of grief, disappointment, and even failure. These feelings may have cast a dark shadow on your first marriage – even down to the memories of planning it.

Because of this, planning your second marriage may bring you flashbacks of your first marriage. For many second-timers, wedding planning also triggers fears of another “failure.”

Solution: Shift your perspective. Throw out the word “failure.” Every marriage is different. Every marriage has successes and challenges. The second time you actually have an advantage: experience.

Even when a marriage ends in divorce, you and your ex-spouse had positive moments and learned valuable lessons that prepared you for your current relationship and will help to make it more successful. And you can learn from your past mistakes and improve the way you handle marital conflicts. Take it a step further by seeking relationship education to prepare you both for long-term success.


Challenge: Your finances are going to change in a big way. Whether you are supporting your new family or you will stop receiving alimony payments, you have to figure out how to adjust your budget while planning a wedding.

Second weddings typically get less help from parents or other family members. Many times, people simply assume you and your partner are more financially adjusted. A wedding is still a wedding, however, and no matter what type of wedding you plan, it’s bound to put a dent in your pocket.

Solution: Before you begin planning your wedding (or, if you’ve already started, as soon as possible), sit down with your partner and have a thorough look at your divorce agreement, your current finances, and what your financial situation will look like after your marriage is finalized.

If you consulted with a lawyer during your divorce, be sure to contact him or her, and review your divorce agreement to prevent any financial surprises. Financial disagreements are a top source of stress for couples, so consider seeking the help of a relationship professional if you have trouble communicating with one another.

Tradition and Rules for a Second Marriage

Challenge: “Don’t wear white.” “Plan an alternative second wedding.”  You’ve heard all of these “pieces of advice” before. Weddings are sacred traditions, and many cultures have different ideas for how a second wedding should be carried out. Plus, you know this from your first marriage: everyone has an opinion about the proper way to get married, and they’re not afraid to share their opinion with you.

Second weddings are especially tricky in this way. Being told what to do, especially by friends and family members who have only had one wedding, may bring up feelings of insecurity.

Solution: The number of weddings you have does not change one important thing: it’s your wedding. Not your mother’s, not your mother-in-law’s, and not the woman working at the catering service you are trying to book.

Most people giving you tips and advice for a second wedding really are well-meaning. But if you start to feel uncomfortable when a person is giving you planning advice, politely tell them that you’ve “done this before,” and you have planned to make your wedding your special day.

Including Your Step-Children

Challenge: You or your partner may have children from your previous marriage. The relationships between you and your future stepchildren might still be a little awkward or even tense.

But this is still your special day, and you want this wedding to be perfect. How do you balance your wedding wishes with the inclusion your future spouse’s children?

Solution: Remember that this day brings you and your partner together, but also creates a union of two separate families. Even if you feel uncomfortable with your partner’s children right now, you will feel more uncomfortable years down the line if they are not included in the wedding ceremony.

Extend a gracious hand to your children and your partner’s children. You can even use the planning to get to know your partner’s children better. It is important, however, to establish your position as a stepparent from the beginning, especially if the relationship with your fiancée’s children is particularly rocky.

This also means communicating with your partner about your stepparent role. Presenting a united front will go a long way to smoothing the path ahead of you. Consider attending family coaching sessions before the wedding even takes place to start off on the right foot.

“Redoing” Your First Marriage

Challenge: No wedding goes perfectly, especially when the memories of your special day are overshadowed by a negative outcome. While you may feel the pressure from friends and family to have a perfect second wedding, you may find yourself setting high expectations and attempting to “redo” your original wedding day.

Solution: You know the stress of planning a wedding already. Reflect on what you could have done better last time and learn from your “mistakes.”

Shouldn’t have made your sister the Maid of Honor? Choose your best friend instead. Spent too much on silverware and not enough on the entertainment? You know better this time.

Rather than focusing on the stress of planning another wedding, remember that this time, you are extra prepared. And keep in mind what we said earlier: no wedding goes perfectly. You will still have stressful moments, just like you did the first time around. But at least with this wedding, you will have a better idea of how to deal with planning mishaps and awkward moments.

Extra Stress May Affect Your Relationship

Challenge: On top of everything you are feeling while planning your wedding, you have to consider your partner’s feelings, too.

If this is your partner’s first marriage, each of you may not fully understand what the other person is going through. And even if this is your partner’s second marriage, you still might not understand each other – every marriage and divorce is different. You might not share the same expectations for your big day.

So how do you get to a level of understanding that will allow you to move forward without additional relationship stress?

Solution: Talk to your partner about attending pre-marital counseling. The months before your marriage are considered the best time to begin counseling. You are facing one of the biggest transitions in your relationship, and you can prevent many (but not all) big arguments by learning tips and tools to openly communicate with your partner and resolve conflicts in a timely and calm manner.


Rooting for you!

Sara Freed


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