Men Tell All: Real Proposal Advice from Guys Who Have Already Gone Through It

We give advice all day long because we live and breathe proposals (and have seen 10,000+ of them), but the truth is, we’ve never really been in the driver’s seat! We, ourselves, have never been the ones doing the proposing, so we thought we’d get some help from a handful of guys who have! Below, we spoke with 5 men (who all bought their rings from our partner and asked them 11 of your most burning pre-proposal questions.

Image 1 of Men Tell All: Real Proposal Advice from Guys Who Have Already Gone Through ItYou can find the emerald ring above here.


Brett: 6 years
Paolo: 2.5
Sam: 2
Tim: 4
Matthew: 1 year, 8 months


Sam: I had no idea where to begin. Each question just seemed to lead to another. Where do I find the ring? When will I have time to sneak out of the house to look at them? Is the 3x-month salary thing for real? Should the proposal be private or public? Wait, I need to find out her ring size—how? It was all so overwhelming.

Brett: Like I am sure many other guys, I had no clue about diamonds or rings or anything. When I first started looking for a ring I went into a name brand jewelry store and while talking to the sales person – it felt like I was dealing with a used car salesman trying to make a nice commission off me. It was hard to feel comfortable going into a jewelry store, I felt like I couldn’t take everything the salesperson said at face value.

Paolo: I started researching about different ring types, the “four Cs” and various different jewelers.

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Tim: I started doing extensive research online and asking friends who recently got engaged. Once I read pages upon pages of reviews, James Allen was the fit for me.

Matthew: My first step was deciding when the best time was to ask the question!


Sam: I made a point to ask her generalities about a ring really early on. To bring it up somewhat naturally, just casually scroll through Facebook next to her on any given weekend. “Hey babe—what do you think about this? *points to screen* Is that…twirly-thing popular?” Play dumb. She’ll take the bait and start answering more questions than you asked. From those few conversations, I gathered the basics. I think there’s something romantically stressful about picking a ring when you don’t know exactly what she wants.

Brett: Melanie and I went into a chain jewelry store while in the mall one day. She picked out a ring that she loved. Then I was able to log onto the James Allen website and find the style band and diamond that Melanie wanted.

Paolo: Courtney once pointed to a picture of a round brilliant solitaire setting in a magazine and said, “I like simple rings like that.” I assumed she liked the round brilliant. I went in to a local jewelry chain just so see what options they had. I felt extremely pressured to buy something due to the “sale” they were running. I explained to the salesmen that I hadn’t finished researching yet and wasn’t ready to buy but they continued to pressure me and convinced me that the ring was a really good value. After another few days of research, I learned that the ring was a horrible deal, and worst of all, the certificate was from some third-rate company. More importantly though, Courtney left her Pinterest logged in on her laptop and I “accidentally” found her private wedding board – every single ring was an emerald cut, not a round brilliant. So, I immediately returned the ring I had purchased and restarted my research, now exclusively on emerald-cut diamonds. Over the course of the next couple days of research, the consensus was that purchasing through an online vendor gave you better value. By and large, most people recommended James Allen.

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Tim: I went with my gut —go with something she will be happy to show off. All I knew was that she didn’t want a colored diamond. I knew her style was unique, classic and that she wanted a large ring because, according to her, she has fat fingers. The easiest and hardest part was deciding on the shape (I ended up picking a pear-shaped diamond) because it was definitely different than most but I was confident she’d love it.

Matthew: I didn’t —I searched and went with my gut. That being said, I looked over A TON of settings and was able to narrow it down.


Tim: I spoke with a couple of friends of mine who recently got engaged or are about to.

Matthew: My fiancé’s best friend and my sister saw the ring, but I had already decided which I was going to buy.

Brett: I am the first of my close group of friends to get engaged so my friends had no good advice. The most helpful advice came from random strangers online (on Reddit) that suggested going through James Allen.

Paolo: No one really. I wanted to ask Courtney’s friends but I didn’t think I could trust any of them to keep the secret. Other than the jewelers at the local chain store (which was a really bad experience), and the James Allen reps via instant message and over the phone (which was leaps and bounds better), I went it alone.

Sam: I had a few friends that also purchased their rings through James Allen — I was initially skeptical of buying a ring online, and they had answers for each concern. I shared designs with close female friends to hear their (brutally honest) thoughts. I also used the various help function on James Allen to an annoying degree—the 24/7 chat for general questions, the diamond-expert chat in which you can share a screen and ask questions about specific stones. One particular employee gave me her email and encouraged me to contact her directly with questions. I hope she didn’t mean it as an empty gesture, because I took full advantage — she deserves a medal for putting up with all my questions.


Brett: I was very excited/nervous. But when I opened the box, I was confident that Melanie would love the ring.

Paolo: I was stunned. I worked with James Allen to customize the setting based on pictures I found on Courtney’s Pinterest. While the drawings James Allen sent me looked nice, they paled in comparison to the actual ring. It was better than I imagined. It was perfect!

Sam: I had it delivered to my office at work, and I couldn’t concentrate all day. Before it was delivered, I just kept refreshing its tracking page. Once it was delivered, it was exactly what I expected —except more impressive. I was super happy, but mostly nervous. I must’ve checked my coat pocket 100 times that day to make sure it was still in there.

Tim: The ring was shipped to my parents’ house while I was in Cancun for work. I was stressed out they were going to miss the FedEx delivery man. Once I opened the box three days before proposing, I was blown away —it made it feel real.

Matthew: Excited! Nervous, but only because the ring was delivered in a larger box than expected (the jewelry box which holds the ring box inside it) and I wasn’t sure where I would be able to hide it!


Brett: I decided to purchase online for a couple of reasons. It was very convenient being able to shop for the ring at my own speed and not feel pressured by a salesperson in-store. I liked the fact that there was free returns and the purchase had a lifetime warranty. Another reason was the price, when shopping at James Allen the pricing seemed very fair. Also, the rings looked great.

Paolo: All of my research pointed to shopping online as you get better value for your money since these vendors don’t have as much overhead as local brick and mortar stores. I was a little uncomfortable at first—not being able to touch and see the ring in person—but it really is so much easier to go the online route.

Sam: I never even considered actually buying a ring online and had never heard of James Allen before this process started. I only visited the site after telling a friend at work about the mental switch (and how I had no idea where to begin), and he pointed to me to another friend who had recently got engaged and bought his ring through James Allen. I was skeptical, but he had a casual answer for every question I threw at him. How could you buy something as important as this without seeing it in person? They have a 30-day return policy. Does there have to be anything wrong with it? No, can be for any reason. Yeah, but don’t you have to pay for shipping? No. Re-stocking fee? No. But how would you know what it looked like? It’s just stock photos, right? Nope—this site has 360 degrees pictures of the actual stone you’d get. What if it doesn’t fit? [sighs] 60-day free re-sizing. After having that conversation, scoping out the website and comparing prices to retail stores, it was an easy decision.

Tim: I didn’t decide to buy online. I decided on James Allen because of their reputation, value and position in the marketplace. Their technology is what made me comfortable with the online purchase.

Matthew: I live in NYC, and I know that diamond shops are generally an overpriced nightmare. I didn’t want to be pestered by sales associates while I shopped. A quick google search brought up James Allen and Blue Nile. I chose James Allen because they could actually show the actual diamond in a setting (Blue Nile only describes it), and because the prices were better.


Brett: Melanie absolutely loves her ring. She is constantly staring at the ring on her finger and smiling, it is great to see.

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Paolo: She cried as soon as I opened the box. So, I feel like I “won” the proposal.

Sam: She ended up crying so hard that she couldn’t actually see the ring. It wasn’t until about 45 minutes later at dinner that she turned to me, jaw dropped, and said “Sam, this is the first time I really looked at the ring—it’s… so” and then started crying again. If she’s ever annoyed at me about something small, I can just say “yeah, but…hey, look at your hand” and she can’t stay mad at me.

Tim: She freaked out and jumped on top of me. She couldn’t stop looking at it. To this day, she is still wow’d by it.

Matthew: Considering she yelled yes *before I even asked* — I’d say she was excited! She still looks at it in the light all the time!


Brett: My biggest question was what kind of ring does my girlfriend like. One day, Melanie and I were in the mall and as we were passing by a jewelry store, I said let’s go in. She went right toward the rings pointed at one she liked and then tried it on. After that, I knew her ring size and the style she wanted. Then I logged onto James Allen and created a ring I knew she would love.

Paolo: Well first I needed to learn generally about diamonds and what to look for. The next question was, where to purchase from. Most independent online resources (i.e., not affiliated with any jewelry store) suggested online purchasing to get the best value. Of those, the vast majority suggested James Allen. And truth be told, I frequented all of the various online vendors (who shall remain nameless) and time and time again, found James Allen’s website the most user-friendly and their staff to be the most knowledgeable, helpful, and the “no pressure approach” was very much appreciated.

Sam: My initial questions about the online shopping experience were answered by my friend who was a recent James Allen customer. After that, the most specific questions about particular stones and bands were answered by James Allen employees through the chat functions. I particularly enjoyed the live chats with the diamond experts because you would share the screen with them and watch them turn the stone and highlight certain imperfections. I liked that they didn’t feel like a sales team. If they didn’t like a stone, they would be honest. See this blemish here? You’ll be able to see that one face up. Hold on—let me try to find some others in the same price range that I think would be better options. It was awesome.

Tim: My biggest question was getting organized and knowledgeable on the 5 Cs (cost is the 5th C).

Matthew: Really just narrowing down the 4 Cs and getting the best diamond that would complement the setting.


Brett: I always knew I wanted to propose to Melanie where we met in our college town, Oneonta.

Paolo: Courtney always wanted to go to Paris — she has some French heritage. So in my mind, I always imagined proposing in Paris at night in front of the Eiffel Tower when it lights up on the hour… unfortunately, my brother proposed in front of Eiffel Tower about four months before I did… so I needed a new idea. The only thing that came to mind was proposing in NYC where we first met. I decided to bring Courtney to the old rooftop garden where we first met during my July 4th party in 2010. I initially lied to her and told her that I had to go to NYC for work. I invited her to come with me to spend the weekend. I had to really sell it — I had to get dressed up for work, get my brief case (which was empty), etc. I then went to my old building and had to convince the doormen to let me bring Courtney to the roof to propose. I asked the doormen if it would be alright if we went to the rooftop for “old time’s sake.” We then went upstairs, took in the view, I gave my speech and proposed. She cried. I won.

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Sam: I wanted it to be private because I knew it would be a very emotional, intimate moment in our lives. I wanted to be able to say whatever I felt her to be able to cry and react without feeling embarrassed so having the proposal at home felt right. I made a scrapbook page for all the different stages of our relationship — each page consisted of pictures representing that stage and a mini-letter from me expressing what that moment meant to me. Each scrapbook page was tied to a balloon, which served as a trail of breadcrumbs leading her to me. I ordered 5,000 rose petals and 150 tea-light candles on Amazon. Her family drove into town and was waiting at a nearby restaurant with my family to surprise her afterwards.

Tim: I always knew I wanted to propose at home and not in a public setting. I told her we were going out to dinner, which was normal for a Friday night. When we were about to walk out I stopped her and got down on one knee. She had no idea.

Matthew: I had tickets to a Rangers/Penguins hockey game at Madison Square Garden (we are both hockey fanatics). Given the importance of hockey to both of us, it was really a no-brainer. So I decided to propose during the game. Plus, I wanted to try to get on the Jumbotron at center ice – which we did!

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Brett: In the days leading up to my proposal, it was all I thought about. On the actual day, I was so excited. Everything I had planned went off without a hitch. It was a great day.

Paolo: I actually wasn’t nervous until the day of. On the day of though, it really kicked in and I started having images in my mind of her saying “no.” I told her that afterward and she told me I was being stupid.

Sam: As you can see, there were a lot of moving parts in my plan. Each night, she thought I was “working late,” but in reality I was either running around to different stores preparing everything (writing the notes, un-peeling the rose petals, etc.).

Tim: Days prior to the proposal I was so nervous I would slip but so excited.

Matthew: We were on vacation in Italy, so pretty amazing! When we returned home, I really didn’t want to act “weird.” We got home late the night before the proposal, so we kept the day very low-key. She is still amazed at how ordinary the day was – at least until the end!


Brett: The best part of getting engaged was seeing how happy Melanie was. We both have been smiling non-stop since getting engaged.

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Paolo: Courtney saying “yes”.

Sam: The proposal itself, and then everything that followed. We agreed not to talk about any wedding planning for at least two weeks, and I am still grateful for that.

Tim: The best part so far has been all of the celebrating and new things we get to do together.

Matthew: She said yes! But other than the obvious, it’s quite funny: Early in the 1st period of the game, my fiancé’s boss texted her that SHE had gotten engaged! So they spent the next 20 minutes or so texting about her engagement … while I sat there waiting (patiently?) for them to finish with their excitement! Admittedly, it gave me the best segue possibly: When I reached for the engagement ring in my coat pocket, I said “Not to steal your bosses thunder…but…” Needless to say, we have a funny engagement story!

And there you have it – 5 men with tons of great advice. As the saying goes, “to know the road ahead, ask those coming back.” Huge thank you to all these men for sharing their journey with us, and to James Allen for making all their fiance’s so ring-happy! Here’s some additional ring inspiration from James Allen as well.

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