5 Mistakes Men Make When Proposing


You would think proposing would be easy. What’s so hard about getting down on one knee and asking, “Will you marry me?” The problem is that proposing is so simple men can’t help but over-think and over-complicate the whole thing until they start doing some very silly things.  If you don’t want to be this guy who hid his fiancee’s engagement ring in a Wendy’s frosty (that she ate), learn from these five mistakes before you pop the question.

Not having a ring

We understand the economy is hitting everyone hard, but you should always have an engagement ring when you propose. No exceptions. If you can’t afford an engagement ring at this time, it’s a good idea is to purchase a more affordable engagement ring and then upgrade the ring later when you’re more financially stable. Find engagement rings bellow $2,000. 

Proposing on an expected holiday

Don’t get us wrong, we love Christmas and Valentine’s Day. But women like things to be special. They don’t want what everyone else has. And what’s so special about being proposed to on the most popular day of the year to be proposed to? That Monday when she goes to work and show off her engagement ring, there will be two or three other women doing the exact same thing. And trust us, she will not like that.

Forgetting her family

We know it’s a little old fashion, but it’s still preferred for men to ask the girlfriend’s family for permission before proposing. You don’t have to necessarily ask her father, but at least let someone in her immediate family know of your intentions of marriage. Here are some more tips on how to ask the father. Also when it comes to the proposal, your friends and family can be amazing assets to help you pick the ring and plan the perfect proposal.

Hiding the ring in weird places

Don’t hide the ring in her food! No, it’s not cute. And yes, she will go to the emergency room. In fact, don’t attempt to hide the ring anywhere unless it’s your pocket. These proposals might seem cute and unique, but they sometimes backfire. An engagement ring is too costly to be tossed carelessly in a glass of wine or baked into a cupcake. Be smart and avoid this mistake.

Telling her you’re “settling”

There is nothing romantic about hearing a long, drawn out speech about how “we’re not getting any younger, so I found you this ring…” Women want to hear that you want to spend the rest of your life with them, not that you’re settling because they twisted your arm about it. If these are your reasons for getting married, maybe you shouldn’t.

Now it’s time to browse for her dream engagement ring!

Does she like expensive things? Everyone is different. Some women are more laid-back while others want the absolute best. If your girlfriend is someone with expensive taste who enjoys designer clothes and isn’t afraid to drop a lot of money on a handbag, then she might expect a pricey ring that’s comparable to the other pricey things that she owns. Check out these beautiful rings for the glamour girl.

Is she plain, more laid back? For some women, an engagement ring will be the only piece of jewelry they will ever wear. These women won’t want a gigantic ring because it will seem too flashy for them. Go for a smaller, less blingy ring for these women.

Is she classic? A lot of women like tradition, and when it comes to engagement rings they expect something classic like the Tiffany setting. The classic ring doesn’t necessarily have to be expensive, but the classic girl definitely expects a nicely sized diamond that sparkles and sits up high.

Does she like large diamonds? Consider what your future bride would prefer: If she cares more about a larger stone than a band, spend a little more on the diamond. If she would prefer a setting that really sparkles, opt for a smaller diamond with a more intricate setting. Browse our engagement ring gallery here to find some inspiration!

Photo credit: Nicole Colwell

Comments (30)


  1. Mags says:

    Actually, seeing as I’m not the property of my father, but an actual adult human being with rights and everything, I’d prefer my partner consult me first.

  2. Tiffany says:

    I don’t think my bf has any intention of asking my dad, but my dad told me recently he wants to be asked…so old school, but I love him anyway. Dad said at least to have the bf talk to him before we announce it to the world. I get it, he wants to know first and let future fi know it’s cool. The same week my mom told me she doesn’t care at all if he talks to her…my parents crack me up. Not like they haven’t already told me how much they love him and would be happy about us getting engaged, whenever that happens.

  3. Kara says:

    Actually, it is not old school for the man to ask the father (or 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. Just think, too, of how the family can joyfully allow that man into their lives as a new son/brother!

  4. Mandy says:

    I think a man should ask the womans father or closest father figure to her. I think its sweet, and romantic. Plus it shows that the man actually has some balls! If he can’t ask my father how the heck is he going to man up and ask me!

  5. Randy says:

    Hey Mags, ease up. Asking the father is simply a gesture that your family matters. You may not like it and that’s cool, but don’t state it like the guy is disrespecting you. It’s quite the opposite. No one thinks you are someone’s property.

    Tiffany, your dad wants one chance to make a point to your boyfriend. He’s unsure about something and he wants to get a word in, that’s all.

    My girlfriends father has three daughters, two who had bad marriages, and he is 70 now and has never been asked permission. I did it for him, and I know my girlfriend respects him so much she will love that I did that. It was a formality out of respect, not a necessity, we are adults and she is no one’s “property”.

    Mandy, I’m with you on the balls. It made a statement to him I’m man enough to stand on equal footing, and also serious about being right for his daughter for the long haul. Proposal is Tuesday in San Francisco!

  6. Ryan says:

    I recently asked my girlfriends father for his blessing. I was soo nervous and kept debating on whether or not I wanted to ask him. This conflict was due mostly to fear of being grilled with questions. I decided that it was best to ask for his blessing. The result: He asked a couple reasonable questions, stood up shook my hand and told me that he really respected me for coming to him first. He said he was proud to have me as a future son in law. Do it guys! Especially if want him to help pitch in for the wedding. This act will make him feel more involved in the wedding!

  7. Joseph says:

    I have a question,I been dateing my girlfriend for 1year 7month’s but the bad part is,she is 17 & Half and i just turned 20 years old.I been very scared of asking her dad for her hand in marriage.What are some good tip’s that i can use.i am really lost because i am buying the ring tomorrow and hopefully this saterdat is the day i can ask her to marry me

  8. elizabeth says:

    I have the most wonderful boyfriend in the world. We live together in our house however our engagement is now on hold due to money issues. I hate that he uses money as an excuse. He absolutely will not get married without a ring or even something that is smaller than he was planning on buying. Since we live together, it’s basically like we’re already married–it only needs to be official. I am 28 and excited to be a mom but am old-fashioned in respect that I believe we should be married first. Now the future (that we talk about frequently) is on hold due to this house we purchased.
    OK, end rant.

  9. alex says:

    To elizabeth – I thought I was reading pretty much about my life. We’ve been together for while and just bought a house. It has cost more than expected so everything is up in the air again. On top of that the boyfriend says he will only think about one thing at a time. At the moment work is too busy, once it calms down he can think about other things. Before that it was looking for a house, buying a new car, not enough money. He said he will propose when he can has the time. I know he will eventually but the need to have anything in place before hand drives me mad.

  10. Natalie says:

    My boyfriend recently proposed to me without a ring, and I accepted because I love him and want to spend the rest of my life with him. However, I was very disappointed that he didn’t give me a ring, but I tried not to reveal this. He told his friends in the UK (he is British) that he was planning to propose to me, several weeks before it happened. Now he wants to keep it a secret from everyone else. We are both over 50, and this will be the second marriage for each of us. I am very romantic and traditional, and having a ring would mean a lot to me. I think his idea of keeping it a secret for now is the reason why he didn’t present me with a ring, because then everyone would know. We don’t plan to get married until next year, after we both retire. Perhaps by then he will be ready to go ring shopping, but I am finding it hard to keep this to myself, so I have told a few famliy members and my closest friend. The first thing they said was “did he give you a ring?.” My answer was “no, but he gave me his heart.”

  11. andy says:

    So you people think i should ask her dad first out of respect and its old fashion, you do know this tradition comes from when you used to buy or offer a cow for the bride. i respect my future wife but i really don’t think i’m going to ask her father considering he thinks he hot stuff because he makes a bunch of money and is really good at his job assembling parts. before my future wife was in a car crash where she almost died he didn’t have anything to do with her and now he wants to buy her stuff and go out to lunch and stuff. and now that the debate about money is over her parents are trying to tell her how the spend it or invest it and I’m trying to inform her and let chose what to do with it. so im not asking him for three reasons hes disrespectful to her hes disrespectful to me and the tradition is based of buying your wife the the father

  12. Joe says:

    I’d agree with the father one in general, it’s respectful and shows you have the balls to ask. However, when the father(as in my case)takes no interest in his daughters life, it’s best to ignore him and just straight up propose. Some people don’t deserve to be respected.

  13. Craig says:

    Does this still apply if her father is not a very nice person, has made no effort with you at all in 3.5 years and acts more like a a horrible boss than a would be family member. Where do you draw the line ?

  14. Badger says:

    I personally see where Mags is coming from and understand her feelings. The tradition of asking the father’s permission stems from negotiating dowry during the days when marriage was every bit as much a financial transaction as it was a social one (if not more so, in many cases!). Young women were–literally and in the eyes of the law–the property of their fathers until such time as they became the property of their husbands. That is a fact that cannot be ignored, even though times have changed. While I know people today do not ask the father’s permission in the same way, that history grates on me and I don’t want any part of it.

    My family means the world to me and I love my parents dearly, but to me, the idea of my boyfriend asking anyone’s *permission* but my own is distasteful and archaic. For one thing, I don’t like that it removes the mother from the equation. My mom and dad raised and nurtured me as equal partners, and they both love me and care about my future. Leaving Mom out of the equation seems very wrong indeed! And what about his parents?

    Taking things a step further: I am fortunate that my parents love my boyfriend and have already accepted him as one of the family, but that’s not the case for everyone–and, contrary to all the songs and movies and popular opinion, it’s not always because the guy is a deadbeat and the nit-witted daughter has been too blinded by love to see it. It could be, for example, that the parents object because he is a different race or a different social class. Perhaps they always wanted their daughter to marry the son of some close family friends, but she went away to college and met someone. There are a million reasons. While you would hope that 1) the parents would honor her wishes and be openhearted toward her choice of a partner, and 2) that their saying no would not actually prevent this young woman from marrying the man she loves, why even open the door for the awkwardness of having the answer be “No!”?

    All that said: we want to honor the respectful side of this tradition. Our plan is simply to ask BOTH sets of our parents, mine and his, for their support of our decision to marry. We like this solution because everyone is included, respectful tradition is upheld, but no women are being marginalized (intentionally or otherwise). In essence, we would love their blessing, but we as consenting and mature adults have already made our decision regardless.

  15. jsfah says:

    I’ve always interpreted asking the parents for their daughter’s hand as asking for their blessing and not their permission.
    Of course, their blessing would put considerable weight on your and their daughter’s decision but intentions are what they are.
    If a man were to ask for my (yet to be born) daughter’s hand I’d expect for him to be assertive enough to qualify his intentions as genuine enough not to require my permission but respectful enough to ask for my blessing anyways.

  16. Anon says:

    My girlfriends father is a jackass, trust me…she would not want me asking him

  17. Jackie says:

    I have to say that I agree with all of these ideas. My father is not really part of my life, but my mother is my closest family and best friend. If my future husband didn’t ask her out of respect, I think I’d be disappointed. This is a time your parents have been waiting for, and dreading. I’m 26, but when my boyfriend talks to my mom, it will still mean she has to let another part of me go, and this eases the transition. Also, mom never wants to be the last to know about life decisions. I definitely agree on the no food thing, how terrible would the night be if you choked on, swallowed, or aspirated your little piece of forever? And I think there is something to be said about having a ring during a proposal. There were definitely times that I’d wished he wanted to marry me so badly he wouldn’t care whether he could afford the ring, or the “one” for me and propose anyway, after 4 years together. But, now that we’re more financially sound, I understand why he wanted to wait. He doesn’t want to settle on something subpar, he wants to know he’s investing in something that really represents how he feels about me, and that’s worth waiting for.

  18. Brooke says:

    My dad has been my rock my entire life. He has sacrificed so much to give me the comfortable and wonderful life I have now as an adult. Even though I am now an independent women who is more than capable of taking care of herself I still expect my boyfriend to ask for his blessing. My dad is still my go to for advice when it comes to every big decision or difficult situation I face and when I get married my husband will have to step up and be that guy. Knowing my dad thinks my now boyfriend can “fill his shoes” and be the number one man in my life means the world to me and I don’t think I could get married without knowing that. My boyfriend and I have been together for almost 5 years and have started ring shopping and seriously talking about engagements and he knows how much that would mean to me and he has agreed it is very important because he respects my dad (almost) as much as I do. As for the ring – he keeps asking me what I want and I keep telling him I want it to mean as much to him as it does to me so I picked out about 5 traditional ring types I like and told him he can add or subtract anything he wants from what I’ve picked to make it as much his choice as it was mine. :)

  19. Justine says:

    I think making the family aware of your intentions is respectful assuming she values their input. If you don’t like her family but she loves them, later in life married or not you will all her to choose between you and her family. That never ends well when she loves them.

  20. lef says:

    I do believe having the families’ (notice the plural) approval is important. However, in my opinion, it’s also secondary. The primary concern should always be the person you intend to spend the rest of your life with. If she (or he) says yes, then you can proceed to the in-laws part. Going to them first is, as others have said, part of an archaic system where women were not treated as human beings. At this point it has certainly evolved past that, in much of the world, but it’s still kind of offensive. Had my husband gone to my parents first I would have felt like he cared more about their opinion than mine. Almost like he’s in it for the in-law benefits more than the wife. If the parents have an issue with their kid’s significant other, it needs to be addressed before the proposal part if at all possible. If they hold their silence all through the dating process then in my opinion it’s clearly not bad enough to believe the couple needs to be split apart, so they should just deal with it. I get along great with my in-laws, and my husband gets along with my parents, so it wasn’t as much of an issue. But if it was? I don’t know what’s worse: happily announcing your engagement to your family only to have them react negatively, or finding out somewhere down the road that they stopped it from happening at all. It’s a betrayal of trust to let it get that far.

  21. Ant says:

    Now opinions please… How about asking her to marry me on our 4 yr anniversary? Good idea or bad? It’s an expected holiday we celebrate and always go out of town for. Also her mother and her have a troubled relationship, should I still ask for her blessing although they don’t speak? Her brother is her closest family member, I wouldn’t mind asking him.

  22. Corey says:

    This is kind of stupid. Not every girl wants a ring, maybe they want something more sentimental. And although it’s like tradition, girls aren’t the property of their fathers. Plus, who says the man must propose to the woman? I’m not even going to mention how heteronormative this is either. Ugh. Also, hiding a ring could be very romantic so please just stop.

  23. Lyndsey says:

    My boyfriend and I have been talking about getting engaged soon. WE moved in together recently and things are going great. When we were talking about I mentioned how it was important to me that he talks to my dad. He gave the most interesting response. He told me that he had always planned on talking to my mom and dad, that he thinks its respectful and that if he is planning on becoming part of our family that he should be able to openly communicate with them. The surprising part was when he asked me to give him and his family the same respect and talk to his parents. I totally agree with this and think that things like this should be more of a two way street.

  24. Melissa says:

    My husband was going to propose to on Christmas but instead we were in the er all day with our disabled son. The day after when we settled back at home he yells from our son’s room hurry and get in here as I hear our son’s machines going crazy I ran into the room both my son and husband laughing. My husband then says to me I asked our son a very important question and he agrees I look over at my son and he has a huge smile. So confused I asked what did you ask him my husband then said we want to make our family complete but before we do that you need to agree to be my wife. I started to tear up I asked my son if it was true and he moved his hand (he has minimal purposeful movement in his hands,arms) to reveal my engagement ring.

  25. Tara says:

    I consider myself an independent woman. I’ve been free of my parents rules for quite a while now. But with that being said, I would like my boyfriend to ask my dad for his permission prior to asking for my hand. Granted, if my dad says no, I’d still expect a proposal. I find that asking is more out of respect as opposed to really asking for permission. I’m a grown woman in a progressive era who expects to make her own decisions. I’d also like to point out that I’m more picky than my own father so… I can’t see him saying “no” anyway.

  26. Josh says:

    I just recently got engaged back in June. My fiancé’s father was a deadbeat dad & her parents had divorced years ago. So instead, I asked her mom for permission (someone that had had to be like a mom & a dad). I know she would not have wanted me to ask her dad.

    It may have, in the past, a tradition on property, but I believe that now it’s a tradition on showing that you have respect for her family & if you are man enough to ask for permission, you will do anything for her.

  27. Priscilla says:

    My boyfriend hasn’t bought me a ring or talked to my father. Not talking to my father isn’t a big deal.I don’t talk to my dad that often. Having said that he could have done a lot better than” we have 2 kids, a house and mortgage so why don’t we make it legal” He could have done better

  28. Cami says:

    I get that this is a ploy. (This is a ring site, after all.) But it’s kind of ridiculous to say “DON’T EVEN THINK ABOUT A PROPOSAL WITHOUT A RING.” Honestly, I think the only “Tip” for how to propose should be “Trust your gut.” My husband and I dated for 2+ years before he proposed. He didn’t have a ring and he didn’t ask my (single) mother. Both of our families had been waiting on the edge of their seats since I moved from big city Texas to small town Montana. They knew we were serious. He knew he didn’t need to ask permission. He also knows that I’m a strong, independent woman and that it wouldn’t matter what my mother said, I would have made my own choice. We had even talked about rings. He wanted to spend thousands on a ring. I didn’t want one at all. He knew if he picked out a huge, expensive ring, I would flip. (He’s the spender; I’m the saver.) So he proposed without a ring and we went to go pick one out together, I got an amethyst ring for 1/10 what he wanted to spend, so he saved some dough and got to put a ring on it and I got to feel special with my unique ring and satisfied that he didn’t the equivalent of a used car’s worth on a piece of jewelry that I’m bound to lose or destroy.

    Every couple is different. It’s ridiculous to pigeon hole people like this.

  29. Kyrstel Knightfire says:

    I don’t have a lot of family left. Honestly, I would prefer he skip this formality and go ahead and ask.
    As for engagement rings, I don’t care what style he gives me. It’s not the ring that matters. I am marrying an amazing man. And that is EXACTLY what matters! Oh how wonderful he is to me!
    Ladies, if the ring is what you are after, go buy it yourself. But if your man is of epic proportions in his Heart and Soul, then wear him! Wear him on your arm, on a date, wear him out, and show him off.
    Ring is nice. The person you want to spend your life with is worth Far More than a rock and metal trinket.

  30. Jess says:

    I am torn for myself because I truly think that it’s Noble for the man to ask the father, on the other hand my father is a blabber mouth and would tell me before the man got the chance to propose.
    So like I said I’m torn…

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