Getting engaged during the holidays with Allison Whitaker from The One Occasion




Many couples get engaged in December, and I think we can ‘blame’ all the romantic festivities and family gatherings for that. If you are one of these lovebirds; hoping to get the ring, or nervously planning to pop the question, keep reading!

Regardless if we are in the middle of the holiday season or on our summer vacation, getting engaged is a big deal in every relationship. So I sat down with an Arizona based wedding and proposal planner, Allison Whitaker from The One Occasion, to chat about how we can help you prepare for this important moment. But let’s take it one question at a time:


How do couples know if it’s the right time to get engaged? 

Allison: It depends on the couple, but I definitely think it’s the right time when you both have talked about it. And you both agreed that it’s the right time to make that next step. People don’t always realize how big of a step proposing is. You are setting up your future to get married, and marriage shouldn’t be taken lightly. 

That’s great advice to talk about marriage before considering popping the question. This will also give you the reinsurance that the answer is most likely going to be ‘yes’. 


How to find out what is your partner’s dream proposal?

Allison: You can do what my husband did, and check my Pinterest boards. That’s how he knew what type of ring I would like.


Do you have any ideas how to pop the question on Christmas Day?

Allison: I think it would be super cute if you have a very large gift box wrapped. But then inside the box there is another box that’s wrapped. And they keep having to open and open until there is the last one, which is the ring box. Also getting a puppy for Christmas is really cute. With a little collar that says ‘will you marry me?’.


What are some of the best ways to incorporate the proposal into the New Years Eve?

Allison: I’m picturing the High School Musical. There is an opening scene, it’s on New Years and they are in a lodge. So I imagine the New Years Eve proposal in that sort of atmosphere. I can just see it happening in front of close family and friends. Something intimate and holiday esque with snow and the mountains would be really pretty. By the way, I am a big fan of New Years Eve proposals, mostly because that’s when I got engaged. 


What would you recommend for somebody who can’t decide between private or public proposal?

Allison: One of the things you can do to get both worlds is if you keep the actual proposal intimate with just you and your significant other. Then plan a surprise dinner and have all the family and friends there for that. This will give the two of you the moment that you need, but then everyone else can be at the immediate celebration after.


When is it a good time to hire a professional proposal planner?

Allison: On the big day you really don’t want to be stressed out. You just want to think about what are you going to say, what are you going to wear, and how she or he is going to react. I always tell people ‘if you can’t manage those feelings on top of planning something, then you should hire a professional or have family and friends help out’. The great thing with professionals is that we do a great job of narrowing down all the details and reaching out to any vendor needed. Like a photographer, hairdresser and or nail salon. I also specialize in setting up or stylizing the day of. So if you have a lot of decor, or want a cute little area set up, I can do all of that. It depends on how large of a scale you are going for.

With social media these days you’re looking at all of these super over the top proposals, but we have to remember that it’s about the love that you have for each other.

It’s important to know your significant other and what is really true to them. As a proposal planner I wouldn’t say that we come up with the entire idea, but I help fine tune it and making sure all of those little details come into play.


I’ve noticed that you put a lot of effort toward planning out what is going to happen after somebody pops the question. As a planner, is it important to not only plan the proposal, but also what is going to happen after that?

Allison: Most of the time when you are excited all you want to do is share the great news with all of the people you love. So I definitely think an element afterwards, either if it’s a surprise engagement party, a surprise dinner, or going on a trip would be great.


What is the best way to announce your engagement to others? Should you change your Facebook status right away?

Allison: I remember my own engagement. The first people I told about it, before posting on social media, were my immediate family. And my really close friends who I wanted involved in the wedding party. FaceTiming all of them is a really special thing to do, because you can show them the ring and they can see the excitement on your face.


What is a healthy distance between getting engaged and starting to plan the wedding? Should couples enjoy their engagement and start planning a few weeks later? Especially if somebody gets engaged during the holidays and wants to get married in the summer. That may not be enough time to plan everything. 

Allison: Ideally I’d say 8-10 months would be a great timeline for the planners, but it just depends on the couple. I know 2020 is a huge year for weddings, so there may be those couples that get engaged toward the end of this year and want a quick turnaround.


Let’s talk about multicultural couples and proposals. What would your advice be if the traditions are different? In some cultures asking for parents approval or blessing is very important. How can we make sure to respect our partner’s culture?

Allison: It’s important to respect your significant other’s culture and know what their background is. But overall respecting people’s parents is a good rule of thumb. Figuring out what would be memorable and respectful to them is something you should follow as a general guideline, regardless if it’s multicultural or not. I think every parent would love a blessing!


Women these days want to be equal with men, and feel that they are valued in the same way. Especially with wedding traditions or when it comes to popping the question. What if the woman decides that she also wants to propose?

Allison: One thing that came to my mind that could be cute, but not over the top, is when you are going through the wedding planning process, and it’s time to buy your fiance’s wedding ring. It could be cute if you would choose the ring and surprise him with a dinner or something romantic


What would your advice be to those who are planning to propose during this holiday season?

Allison: Remember who your significant other is, and what is the best for them. If they want something super crazy and public, like a proposal on the big screen at the football game, or they want something intimate, just the two of you at dinner. Remember what they care about, what their core values are. 

Also, hiring a photographer is one of the most important things you can do for that event, because it’s something you want to remember forever! I know iPhones are turning out to be pretty great these days, but I promise nothing is better than a photographer who knows how to get good angles and get that shock factor.

It’s never a bad idea to seek professional help, or help from friends and family when you are planning something so big. Other people will always have great ideas as well. They will help you refocus or fine tune little details that you are not thinking about.


Connect with Allison Whitaker:

Instagram: @theoneoccasion





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Although I was born in Serbia, graduated in Italy and have been living overseas for 14+ years, I'm very proud of my Hungarian heritage.
I love documenting my life adventures, trying out healthy recipes and herbal remedies, or going on family trips in our new home, Canada.

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