#ItsDateNight with Anna of Niagara Proposals

niagara proposals

We’re sitting down (virtually) with some amazing Canadians who are dishing on all things datenight. From their own first date stories, to dating pet peeves, a look into their businesses, advice, and more!

Who they are

Meet Anna Katherine – the owner of Niagara Proposals & Proposal/Event Planner Extraordinaire! 

AK: I am an industry geek on all things weddings, events & hospitality and I love making peoples best days & dreams come to life. I have a diploma in hospitality, 3 wedding planning certificates, and I currently also manage weddings/events at a venue in Niagara.

I have over a decade of experience now, and I love making big moments even bigger.. I have always had a huge passion for celebrations, socializing, and the 3 things that are universal to everyone – food, drink & of course, love lol!

“I like to think that I have one of the best jobs in the world, I get to create and witness the happiest days & moments people dream of for their whole lives. I am so grateful I fell into a passion that is stressful & a lot of hard work but so rewarding.”

I started my own business this year – Niagara Proposals due to one of my great mentors leading in me in the right direction (shoutout to Nicole Harris from LA!) because my ultimate life goal is to one day be a luxury wedding & event planner (including proposals too), I want to expand my services in the future and am starting with how most great weddings start – with engagements! I’ve always been extremely ambitious and had a very entrepreneurial side to me so I’ve always known I’d be a business owner and that I’d have my own thing inside the industry I am passionate about. So, it feels really good to finally be doing what I love to do and so right now – this is just the beginning for me and I can’t wait to make more people’s dreams come true!

Lets talk love languages, what’s yours?

AK: My love language is actually Gift Giving & Acts of Service – which initially can have some negative (materialistic) sounds to it but it’s actually more about when someone thinks about you and picks up a small token that reminds them of you, or when they care so much to make you smile with simple things like making the bed or doing the dishes, etc. – it goes back to “it’s the thought that counts” mentality.

For example, if my boyfriend brings home my favourite snack, I feel so loved by it, even if my best friend gave me a rock she found on the side of the road that reminded her of me – I’d probably cry as it’s just nice to know someone is thinking of you. 


I think this actually helped develop my passion for proposals, weddings & events as I value so much when someone thinks of you or goes above & beyond to make a moment special and so I absolutely love to do it for others. I have always been the one planning my friends’ birthday parties – making them super extra or even when I plan/work in weddings – finding the little things to make the moments just a little bit more special.

A good example was a wedding I planned last summer and their favourite drink was a Negroni so we had spent months discussing Negronis and cocktails throughout their appointments… so I made sure that I gifted them a bottle of Campari at the wedding – it was the only physical gift on the receiving line but I am pretty sure they finished the bottle on the honeymoon, lol! Or another one was when a couple told me on their first date they ate chicken fingers & fries so it became their favourite dinner together so on their wedding day I made sure they got served their meals as well as a plate of chicken fingers & fries – they loved it and thought it was amazing I even remembered haha!

It can be something so small and so casual but it’s always fun and rewarding to find ways to make things as special & memorable as possible. 


About first dates…

AK: My first real date with my boyfriend was actually a date night in Niagara Falls, we were 15 & 16 at the time (yes – we are high school sweethearts) but we did the whole ‘act like tourists thing’ and got a fun pass and ran around like we hadn’t lived in the area for years, we went for a romantic meal, rode the Skywheel (caught the fireworks on it too), had a photoshoot in the wax museum and I am pretty sure we laughed all night long, it’s one I’ll always remember. Also because the photoshoot in the wax museum created some pretty embarrassing photos LOL! 


Today, my ideal date is definitely almost always focused around food and drink, we are big foodies and love to explore restaurants and also love to cook. So we normally try new recipes or new places, but I also love when we do something more adventurous and experience new things together. The best nights are when we have a great meal, awesome drinks & find a new activity to do – like new board games, go karts, wine tasting, or maybe like a hot air balloon ride would be cool. 


For those who are thinking of popping the question soon, what are some hot trends right now?

AK: Right now, it’s definitely the bigger the better! I feel like with social media, people (the proposers) are realizing they have access to so much opportunity. They can really make the moment as big/memorable as they’d like and include things like giant “MARRY ME” letters, 100s of flowers and candles, a live violinist, a hotel with a view or anything they can imagine, even a trip can be included – a planner is the one who can find all these things for you and create the vision, plus they are great secret keepers, lol. 


The biggest trends I see currently are unique “MARRY ME” signage, lots of rose petals & for sure having both photo & video on site hidden away. 

What are your favourite local date spots?

AK: My favourite spots change often depending on the season but I’ll let you in on some of my ultimate favourite local secrets in Niagara right now.. Taris on the Water (Welland), Cured Charcuterie & Cocktails (Font Hill), Twenty & N’ata Cosa (St. Catharines). Niagara to me is the foodies hidden gem in Ontario and there are sooo many good restaurants all over the region to check out.

What inspired the “Send a Hint” service for Niagara Proposals and how does it work?

AK: The send a hint feature was actually inspired by a close friend of mine who has been waiting for her ring for about a year now, I was telling her about my proposal planning services and she said that’s great but I don’t know when he is going to do it, can you just send him an email to push him in the right direction? And LIGHT BULB, my brain started spinning with ideas. 


Essentially you go here, fill out the form at the bottom which will sign you up to my regular mailing list (lots of date night inspo & other goodies) and signs them up to receive the hint email. The hint email is completely anonymous and says “Someone sent you a nudge, wink – wink – is it time?” and includes a bunch of info on my services, explains how proposal planning works, why it will be useful, some inspiration for them and that their SO is awaiting their ring… it hints that it’s coming from a family member, friend or excited coworker who can’t wait to be the ultimate wedding guest but doesn’t reveal who signed them up so anyone can do it for anyone who needs to pop the question asap. 


It’s a cute and fun way to tease your friend or SO in my opinion. 🙂 


What’s your favourite part about what you do?

AK: My favourite part is the proposee’s reaction, they are always so shocked & happy, my second favourite part is designing the visions and seeing them come to life. I’ve always loved this part of planning!

Proposal recommendations…

AK: My proposal recommendation is don’t be scared to even message a planner like me for help!

I offer full service planning which is the whole experience but also a concierge style service where I can help by guiding you in the right direction. And for a spot reco, I always guide my clients to pick a place that is a part of their love story, finding those ways to make it as meaningful as possible!


Now a question from our new datenight game!

Would you rather plan for a vacation months in advance, or travel spontaneously?

AK: OUU THIS IS TOUGH FOR ME!! Being a planner, I am going to say months in advance as I like to learn as much as I can about a place to ensure I get to do all the things but am also so totally DOWN for a spontaneous trip anywhere right now, like take me to Bora Bora – tomorrow? OK LETS GO, I’ll research activities on the plane lol!!! 

So I am going to go with both.

Anna shares a lot of fun inspo on her Instagram, be sure to check it out and follow along – there’s much more coming up this year from giveaways, collabs with other local businesses, wedding and event service, and more!