How to Propose to a Girlfriend that Knows You’re Going to Propose

Letting the cat out of the bag and having your girlfriend find out when, where and how you’re going to propose is a classic mistake that I see men make all the time.

Of course, this situation is completely avoidable. There are ways to make sure your plans aren’t leaked in the first place and I cover this in excruciating detail in the book. I also cover creative ways to throw her off your scent without pissing off your girlfriend (since she’s now expecting a proposal and it’s likely her friends/family also know about it too, which equals more expectations).

This young chap’s solution is one of the ways I highly recommend – have a back up plan and create diversion tactics. (Maybe he read the book?) lol. I should also point out that he did a lot of things right in his proposal that many men fail to overlook, such as having secret videographers set up (via friends and family) to record the proposal and making sure it was a meaningful proposal by revisiting the places that were significant to their relationship.

Click the video below to watch how this guy handled proposing to his girlfriend who found out he was going to pop the question.


New Research Ties Women’s Unhappiness with Proposal to Race

small_wow_proposals_info_graphic_New research by proposal expert, Robert Gosling, suggests a man’s race may be a contributing factor for whether or not a woman can expect to receive the proposal of her dreams.

Today, I am revealing new research that sheds interesting light on the recent leap in the number of women unhappy with their marriage proposal (25% to 33% from 2011 to 2013).

With uber romantic and over-the-top proposals being de rigueur on YouTube and many becoming overnight sensations, like the home depot, and flash mob videos that made news headlines nationwide, it would appear more men are getting the message that a proposal should be a big deal and are doing their best to make the moment memorable for their intended.

Why the growing discontent amongst women then? According to the research, certain segments of the population have yet to realize the shift in their mate’s expectations and are skewing the numbers down.

2000 married women were sourced for the anonymous study in New York City over the course of a week. Each subject identified their mate’s race, and were asked to rate their marriage proposal as either satisfactory (they were not disappointed with any aspect of their proposal) or unsatisfactory (they were disappointed in some aspect of their proposal).

The disparity was astounding.

47% of women proposed to by Black men rated their proposal as unsatisfactory

35% of women proposed to by Hispanic men rated their proposal as unsatisfactory

29% of women proposed to by Asian men rated their proposal as unsatisfactory

26% of women proposed to by White men rated their proposal as unsatisfactory
Many women proposed to by Black or Hispanic men complained of proposals that were rushed or ill-planned, diamond size, feeling like their men waited too long to pop the question or were only asking because of extenuating circumstances. Women proposed to by Asian and White men were disappointed in the place or location of the proposal and that it wasn’t romantic or original enough.
While the sample size is small, there is something to take away from the results.
It is clear that all men need some help in this area, but Black men and Hispanic men particularly need to step their marriage proposal game up, at least in New York City.

Proposing on a Holiday without screwing it up

holiday proposalAh, the inevitable question that will plague your mind once the decision to actually jump in with two feet has struck. Is there a better time of year than others? As it turns out, Christmas is considered one of four big proposal days, along with Valentine’s Day, Thanksgiving and New Years. Thirtynine percent of proposals occurred between November and February among 20,000 newlyweds surveyed by the popular wedding website Of those, 16 percent got engaged in December,more than any other month, according to TheKnot editor Anja Winikka.

One can see why, given many of these holidays are considered the most “wonderful” (Christmas), “romantic” (valentine’s day), “family oriented” (Thanksgiving) and “celebratory” (New Years) time of the year and all. It would appear another reason for the popularity of tieing a proposal to a specific holiday is knowing you’ll to be around family and surrounded by all the people you would want to see and share your exciting news with. All valid arguments, but I’m sorry to say, when stacking the pros and cons, the cons vastly outweighs any reason to follow the lead of other guys. Just because a lot of men do this, doesn’t meant it’s right. After all, if all the men jumped off a bridge while proposing, would you do it too? I kid, but as you hopefully realize by now, most guys don’t really know what they’re doing and their unhappy girlfriends are a testament to this fact. Trust me, I only want to spare you as much pain as possible. Although I wish you and your wifetobe a long and happy life together, like ever after if at all possible, I want to protect you from the consequences that could occur should, worst case scenario, you  don’t work out. I hope my advice will never have to apply for you, but it’s better to be safe than sorry, right?


Here’s the thing with proposing on a holiday like Christmas, Valentine’s Days, or even the Fourth of July, for that matter. As sweet as the sentiment is, heaven forbid you and your sweetie decide to part ways three, five, seven or ten years down the line. Should that happen, that day and what it represents, will be tainted in you and your girlfriend’s mind forever. You and your ex will have a lifetime of misery when that particular holiday rolls along, and it will come like clockwork every single year to break your heart all over again. You won’t be able to stop yourself from recalling that fateful day when you proposed, while everyone else around you is in the throes of celebration and happiness. If the proposal had been on any other day, then the probability of remembering the date and getting all torn up about it, is slim to none. Zilch, really. I don’t say all of that to say go into your marriage thinking it might fail. I just want you Another reason popping the question on a holiday sucks as an engagement day is mostly because so many people get engaged on the same days and an engagement should be a special day in and of itself, not shared with many other “special days” or a holiday. You see, there are guys who propose on a holiday, like Christmas, and the proposal “story” consists of him giving the “gift” of a ring to his fiance.Everyone knows that if you’re born around a gift giving holiday, people will try to screw you over with one gift instead of two.


Besides being pretty cheap and unimaginative, everyone else she knows will have received a gift. Putting a ring under a Christmas tree does not constitute as “planning” a proposal, it’s called giving a Christmas gift at the expense of a separate Christmas gift. My advice is to elect a date that isn’t tied to anything else, and make it your special day. For example, a random weekend in the Spring, when the weather is projected to be beautiful. Try to avoid proposing on a vacation to your favorite place in the world that you visit every year. Much like proposing on a holiday, if you propose in New York City and your relationship never takes a wrong turn, every time either of you visit or are reminded of the city through advertisements or movies you will remember the proposal by association, awakening those warm fuzzy feelings.

However, if things don’t work out, many things can go wrong on a

holiday. In this environment you will not be able to plan ahead and

scout out the perfect location. Often places are not how you

imagined them and often you cannot get access to when you had

planned in your head, that said if you are diligent and do your

homework you should be able to pull it off.

Should I ask for her Fathers hand in marriage?

Angry FatherThis may seem as outdated to some men as dropping down on one knee, but nine of ten women want you to have sought her parents permission before asking her to spend the rest of her life with you. That’s 90% of women, or what you would call the overarching majority.

Then, where did this idea come from that guys don’t have to or shouldn’t go seeking the parents’ blessing before asking for their daughter’s hand in marriage? It’s just a hunch, but I think perhaps it’s just the loudest women who shout it from the rooftops that they It is your job to ask or to find out if this is important or offensive to her. I hate to generalize, but the only women who seem to get offended and angered by a man asking for his girlfriend’s parents’ advice, are feminists and very alpha type women. If you’re not familiar with the term alpha woman it’s usually only used to describe men I’ll break it down for you. An alpha woman is the dominant woman in a group. She is typically assertive, powerful, strong, confident, and a big earner. She likes to be on equal footing with men and doesn’t want to be seen as a “weak” or “needy” woman. She’s very independent, and thus the idea that you need to clear things with her father or parents does not appeal to her, as she interprets such actions being owned and needing clearance.

It is tradition and remember you are not just marry her, you are marrying into a family. The father is considered the “covering” that the daughter is under. For that matter, it shows complete respect and honor for the man to ask first. Do not take that moment away from your future father in law as this might build a little resentment. Dad has always expected from all of the fiancee’/husbands of my sisters. Besides, to me it shows that the person is mature enough to do the respectful and right thing even if it’s hard/scary to do, which is always a plus! It lets the bride know that her fiancée has thought this through and that the groom has her daddy’s approval. Giving them both confidence that this a positive step in their lives.

If you do not have to courage or respect to ask her parents permission this does not reflect well on how you see the relationship .If her father says no, which is unlikely if she’s over the age of 21, ask her anyway. He cannot stop you, and you will be the better person for it.If your girlfriend does not know her father or he has passed, you can ask her mother or the closest male figure in her life instead.

How to Propose the Right Way

who's finger is it anywayOne of the cardinal rules of buying a ring for your future wife is to never let another person try it on before she does. Be careful because anyone you show it to will have a desire to put it on their finger to see how it feels to wear something so beautiful. You will hear phrases like:

“It won’t do any harm,” or “She will never find out,”. If you do not ignore these warnings you will be playing with fire.

For example look at it this way, you arrive home from work and your girlfriend has surprised you with a Ferrari. Wow that would be amazing, you would feel very impressed and would love to return the gesture. Next, her brother comes to visit and tell you her took it for a spin before she gave it to you. Boom the gloss is suddenly taken off the experience. The same rules apply to a ring.

The reason why its not okay isbecause if you are giving it to her, it is hers and hers to share who with and when. Its not your place to decide who gets to give her ring a test drive. She will later gladly show off her ring and offer to others to try it on.

Another less obvious reason and somewhat rare one is if one of your friends or even yourself is tempted to try the ring on your little pinky. You might not be able to take it off again. Rings are made for little feminine finger and are not designed for a a mans hand. Engagement rings are especially expensive, delicate and can be damage easily.

Another humongous mistake, even worse than allowing any of your friends to try on her ring, is to recycle a ring that you gave to an ex-girlfriend with your current one. Usually second handed rings mean bigger gems, better settings, and fabulous prices, but giving a ring you picked out, based on your ex’s tastes and preferences, to a completely different woman is not only creepy and tacky, but stingy.

She’ll wonder if you simply chose her because she had the right ring size. Furthermore, your actions will not be a good sign of things to come will she always get sloppy seconds? It screams that you couldn’t be bothered, even if that wasn’t your intention.

For example, perhaps you consider the ring as a token of your intention to marry more than anything, or maybe you couldn’t afford a new ring after shelling out thousands of dollars on the old one. I see where you’re coming from, but in the former situation, most women simply won’t agree with you, and in the later situation, where you were lucky enough to get the ring back from your ex, pawn it or sell it online or back to the jewelers. Then use the sales to fund your new girlfriend’s ring.

There’s no need to hold on to a ring from an ex who denied your proposal for marriage, unless you are doing so because your ex has passed. Still, most women just won’t be comfortable with the idea of wearing a ring meant for another woman, unless it’s a family heirloom.

Why would she want to wear a reminder of your past love for another woman and constantly wonder if you would be with her if your ex hadn’t said no? So, even if the chances of her finding out are slim, do right by your girlfriend and give her the same respect you’d want her to give to you.

Whose Proposal Is it Anyway?

questionmarkA big question you are going to find yourself facing at the beginning of the planning stage, is what activity, event, and/or location you should choose that will resonate with and appeal to your girlfriend.

You want something that she’ll find cool, unique and interesting, right? Well, most guys say that’s what they want, but somehow along the way end up planning a proposal that they think is cool as opposed to something she would love. I’ll expound more later on why this is one of the worst places you can propose, but the majority of the men who propose at sporting events do so because it ties into their interest and passion, not hers.

Even if she is a huge sports fan, this is one time she will want the day or evening to be all about her. Proposing at the game reeks of trying to kill two birds with one stone. No bueno.

If your aim is to deliver a perfect, storybook proposal that would make a harlequin writer proud, your job is to think hard about the things that your girlfriend loves, and remove yourself from the equation. Start by asking yourself the following questions:


Where has she always wanted to go?

What has she always wanted to do?

What are her hobbies?

What would be different from the mundane?

What’s her favorite musician/artist?

What have you been talking about doing forever?

What has she been trying to get you to do forever?


Make a list and start looking into the options that are feasible, within your budget, and would apply to whether she wants a public or private proposal. If you can combine elements, do so. Don’t be afraid to pack it in.

For example, if she has a personality that lends itself to a more public proposal, has been wanting to learn how to tango for ages and trying to convince you to do it with her, you could surprise her with a tango dance lesson. Coordinate with the owners of the studio to have you both take the center stage towards the end of the class and play your favorite song in lieu of the tango music. Recite your speech and propose. Celebrate afterwards at a restaurant she has been dying to try with some close family and friends.

If you notice in the example above, every thing that you have chosen to incorporate in your proposal is centered around your girlfriend: her desires, what fits her personality, what is important to her. Don’t forget this day is about elevating her and making her feel super special, not about your desires, what fits your personality and what you have always wanted to do. If you get this right, you’ll be golden.

Ignore this rule at your own peril.