6 Common Wedding Planning Dilemmas

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Photo by Aaron Delesie

This article originally appeared in Party Slate | Author: Jessica Terson

Consider a magic trick. The magician pulls a rabbit out of his hat, while onlookers ooh and ahh over the seemingly impossible feat. The perfect wedding, like the perfect magic trick, requires having a few tricks up the sleeve. Bespoke event planner David Pressman of David Pressman Events sat down with us to share how the right wedding planner can solve six common wedding planning dilemmas. From getting guests to RSVP on time to making sure the bridal party stays on schedule, Pressman shows us how wedding planning can be stress-free —  at least for the couple getting married. 

Wedding Invitations —

The Buck Stops Here


1) Getting Guests to RSVP

Photo by Laura Bailey

The days of handwritten letters are long behind us. In that light, it’s no surprise that guests sometimes forget to RSVP. As a full-service event planner, Pressman takes on the responsibility of creating a master spreadsheet that lists important guest information. He will individually contact each unaccounted-for guest to fill in any missing information, whether that be a simple “Yes I can attend,” or “Oops, I forgot to add a food allergy to my menu selection.” For Pressman, this isn’t an extra service but an essential way he can help alleviate stress for his clients.

2) Addressing the Plus One

Photo by Jessica Rieke

Consider the scenario: You’ve addressed an invitation to your cousin and only your cousin. A few weeks later, your aunt calls you to ask if your cousin can bring a plus one. This is where an event planner like Pressman steps in. Pressman will ask his clients helpful questions like, “Are they engaged? Do you socialize or have a relationship with them?” If his clients prefer not to budget for an additional guest or invite someone that they don’t have a relationship with, then Pressman will personally decline the guest’s request. Because Pressman is the only point of contact that his clients will need for planning their wedding, his job includes answering any of those tough questions posed by event professionals, friends, or family.

Bridal Gown Shopping — When Everyone Has an Opinion

3) Keeping the Negativity at Bay

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Photo by Ana and Jerome

Let’s be honest. Shopping can be stressful. Now imagine you’re standing up on a platform, surrounded by family and friends, trying on what you hope will be the perfect dress for the most important day of your life. Suddenly you hear your mother say, “I’m not sure if that dress suits your arms.” As Pressman reminds us, everyone has their own agenda when it comes to finding the right wedding dress. While a mother might have the best intentions, it’s also likely that she still sees her daughter as a little girl who should or should not wear certain items.

Pressman helps his clients avoid uncomfortable shopping scenarios by offering to take them on a one-on-one shopping trip. This gives the bride an opportunity to try on a variety of dresses and experiment with different styles in a pressure-free (and opinion-free) environment. Pressman is also willing to join the bride at later fittings when other family members or friends might be in attendance. By this point, he will have met his client’s loved ones and feel comfortable diplomatically navigating the situation.

4) Choosing a Trusted Designer

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Photo by Ana and Jerome

Bodies are like snowflakes; no two are the same. Finding the right dress means finding the right fit and style. When you walk into a store, you want to know that the person attending you is a professional that you can trust. Pressman’s own professional history in the fashion industry perfectly positions him to be helpful and he often takes his clients shopping at stores where he knows and trusts the brands. A representative for Oscar de la Renta, Vera Wang, or Monique Lhuillier, for example, has a professional career in designer clothing and they want their clients to look their best and will never sell something just to make a sale. A great event planner will also know how to find other required event professionals — be it a florist or caterer. When it comes to planning weddings, Pressman makes sure to narrow down an event professional list that will specifically meet his clients needs.

Hair & Makeup Scheduling — Starting the Day Without a Hitch

5) Wrangling the Wedding Parry

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Photo: Laura Bailey

For a bride on her wedding day, getting ready with her bridesmaids is a great joy. It’s a chance to drink champagne, share stories, and indulge in a bit of pampering with her best friends. What could possibly go wrong? 

While larger bridal parties spare a bride or groom from making the difficult choice of whom to include or exclude from the list, they often require extra attention. Larger bridal parties may need more than one room for hair and makeup preparation. Consequently, bridesmaids or groomsmen may feel hurt if they have to get ready in a different room than the bride or groom. When multiple hair and makeup event professionals are used for larger bridal parties, there’s also a risk that some will want to switch stylists. Pressman knows there’s no time for the bride or groom to deal with these stressors. Again, using his diplomatic skills, Pressman will individually speak to any injured individuals and explain to them that they’re “working backwards from a biblical timeline — down to the minute.” He will even share the schedule with them, reminding them that timing is everything.


6) Timing is Everything 

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Photo: Gloria Mesa

As Pressman reminds us, bridal parties often don’t realize that event planners are working backward from a timeline. If the ceremony starts at 6 p.m., then photographs might take place at 4 p.m., which means the bridal party needs to be ready to go by 3:30 p.m. 

“Imagine scheduling 12 people in two different rooms in hotel or venue,” Pressman says, “and then you get a call the night before and the sister comes up and says I can’t do that time.” While 75-percent of the time, Pressman can rearrange the schedule to make it work, sometimes he has to sit down with the individual and explain the reason why the schedule is set up a certain way. “People often understand things if they have a moment to see the big picture.”

The bottom line — a big part of being a premier event planner is being a diplomat. For a bride or groom, having a bespoke event planner to navigate the obstacles can make all the difference.

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