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Dear Captain Awkward

I have been with my partner for over 5 years now, and I love him to pieces, I can’t imagine my life without him, but I am scared that if I propose to him he’s going to say no, from what I know we are very happy, and I know that he loves lots of ‘girly’ things as well as ‘male’ things, wearing dresses, cosplay, ribbons, romantic comedies, video games, and shoujo manga.

I thought it would be a great Idea to propose to him later this year by taking him to the largest convention we have in the UK for a romantic weekend away, wine-ing and dining him, I’ve booked the hotel room, saved up nearly all the money I need and bought a ring and a Tardis ring box to put it in.

But I keep second guessing myself now, thinking what if he wouldn’t want me to propose to him, or at the least having no idea what I would say, would he feel weird about his girlfriend proposing to him, I mean I’ve asked him in the past and he always said he hasn’t had a problem with it, but since I’ve started researching how to propose as a woman, I’ve found so many posts saying just not to do it, that it takes something away that is solely for the man to do, that I’d be robbing him basically of him being able to do it and that I would emasculate him by proposing to him, that he would become a laughing stock amongst other men. Despite reassurances from his and my male friends that if their own girlfriends proposed to them they’d be ecstatic, and they think he would be too, since he is not a traditional male.

I want to propose to him so much, but in doing so would I just humiliate him?

Yours sincerely

Dearly befuddled

Dear Befuddled,

How exciting for both of you! Two thoughts:

1) After happy five years with someone, surely a discussion of “do you want to keep doing this”/”should we formalize this thing we’ve got going on in one of the ways open to us under the law” is not a completely foreign one. The saying of the question in so many words, the presentation of symbolic gifts, etc. might have an element of surprise involved, but the prospect of the decision is surely not a surprise, right? If it is, then maybe a “Hey do you ever think about wanting to get married someday? How do you want us to go about making that decision” conversation before the whirlwind weekend is probably in order. If he has strong feelings about where and how and when this should all go down you’ll find out about them.

2) Someone who would not want to marry you or who would be humiliated because you were the one who asked the question, someone who would poop all over the awesome thing you’ve planned because: Traditional gender roles! is probably not right for you on a number of levels.

It sounds like the worst thing that could happen here is that he is like “Yes of course, let’s get married. Though I had this awesome surprise planned for you” and you say “we’ve got the rest of our lives to surprise and delight each other, you silly gorgeous man” and then you kiss a lot and get married some day.

Go live your awesome love story without fear or apology!

Edited To Add:

While we’re on the subject of lasting commitment, an Awkwardeer is seeking help with their wedding vows.

Hi Captain!

I love your blog, and the direct approach you have with words and creating good space for oneself in a relationship. My question is of the happy problem variety … I’m getting married at the end of May to a fantastic guy, and am looking for advice on building a strong marriage (and some inspiration as I start to write my vows).

We’re in our late thirties and have pretty similar romantic histories (very few relationships, none of which lasted very long), which means that we don’t have a lot of personal experience with the ins and outs of long term relationships. Our approach has been to “use our words” as much as possible, and while we don’t always agree, I can’t think of anything that has turned into an actual fight. (We’ve both wondered if this will create a problem at some point, but haven’t been able to imagine it.)

So. We’re getting married (hooray!). And I’m really interested in your (and the awkwardeers) thoughts on maintaining and keeping a strong partnership over the next (hopefully) 50+ years.

Thanks!

What makes love stay? Got any favorite poems or quotes or readings? LET’S CYRANO THE DE BERGERAC OUT OF THIS.

 

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Dear Captain Awkward,

I’m a white ciswoman in my late twenties living in the Midwestern US. I’ve had a free online dating account for a while, having marginal success with short term dating but nothing that’s really led anywhere. My only *serious* relationship ended five years ago, after less than two years. I’ve come to terms with being choosy, and I don’t think that’s a bad thing, but more recently I’d started to wonder if I was being too picky or not patient enough or something. However, this latest guy has me all excited and fluttery! However, he’s got some baggage that has me confused as to how best to behave.

During our back-and-forth he was friendly and engaging, we got on quite well, and even realized we had a female friend in common (which was like an instant recommendation). We’ve only had a few dates so far, but we seem to be clicking really well and it feels like I’ve known him much longer. I was already be a bit nervous about too-much-too-fast (scaring him off?), when he told me (over a few conversations) that he’s in the process of a divorce that’s ending a marriage of mutually-destructive maybe-verbal-abuse and disillusionment over their shared religion, and the split was less than 6 months ago.
 
(I know that some cheaters use “getting divorced” as a cover, but given our mutual friend, his social media profile and his dating profile, as well as my gut, I believe him)

I am not sure what I should be doing given his situation. He’s voiced worry he might be using me, and while I don’t feel used, I worry he might mean using me emotionally as a rebound (is a “rebound” even a real thing?). Ideally, I would be there supporting him to help him work through what he needs to work through for us to have a great and fulfilling relationship that lasts for a while and leaves both of us happier, but how wishful is that thinking? I worry that being in too much of a caretaker role would get in the way of being seen as a romantic partner, but should I worry? And mightn’t moving too quickly romantically lead to relationship collapse if he’s not as ready as he thinks? Can you help me balance my desires and his potential needs?

Sincerely,

Wishing it would just work!

P.S. I don’t think it matters to him, but he’s in really good shape compared to me, so I also have that frustrating but common worry that he’ll suddenly notice and not find me attractive anymore, which is definitely contributing to my fear about coming across as too much of a shoulder-to-cry-on or too maternal.

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Dear Captain Awkward,

I have a pretty simple question. How do I nurture my own sense of romance?

A bit of background: I’m a twenty one year old queer girl. I was born in Mississippi, though I spent my teenage years in the north east. I’ve never dated a girl because of my own issues with repression. I’ve hooked up with girls, dated guys, and hooked up with guys. I’ve spent alot of time trying to be romantic guys, and have come to a place where I’m really happy with the friendship and sex I have with guys. (Yay!) I know thought that I want to be romantic with girls not guys, though, and I’m really confused on how to go forward with that. Let’s just say that all of the angst, self repression, disappointment, and forcing hetero romantic situations have left me a bit bitter. I’m not sure how to get what I want or even talk about what I want. I’m spent so much time being bitter and violent towards myself.

I’m basically just talking to girls I like and using the “you’re a person I’m a person maybe we could interact in awesome romantic people ways” rules to muddle through. Any advice on how to muddle productively? Do I basically just have to accept that I’m going back to being say where I was at fifteen with guys? On top of this I have the problem of not finding mainstream depictions of romance desirable- its all so based on magic and love fixing everything. Do you have recommendations for art that depict romance in a more nuanced and awesome way?

Onward latebloomers!
gallant_girl

Hi Gallant Girl, Elodie Under Glass here. This question! This is the sweetest question! Gallant Girl, it is so nice to hear from you.

Unfortunately, after the Captain gave me this question, I sat on it for four months. I discussed it with my friends while drinking wine in the Netherlands: “Where does romance come from? Particularly the kind of romance that we practice.” I asked friends who review books and friends who write books and friends who read books:  “What art depicts romance the way that we live it?” I asked queer friends, married friends, married queer friends, friends-with-kids, and people that just looked interesting. I started to lunge at people out of mailboxes: “HELP ME WITH THIS QUESTION ABOUT ROMANCE.

“How about Malinda Lo?” people suggested, “She did a thing. Or that movie where Piper Perabo and Lena Headley hold hands.”

“True, they’re good enough in their way, I guess,” I’d reply, “But I want, like, queer Dorothy Sayers banter, I want Tipping The Velvet but with a happy ending, I want stuff that isn’t stereotypical: I want stuff that will cheer Gallant Girl up.”

People said “Catherynne Valente! The L Word! A television show with dogs in it!”

All of which are wonderful but none of which quite touched the thing I wanted to tell you: that you’re right, that you should stop worrying if you can, that you’re doing pretty well.

 

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Leslie Knope holding a big binder that says "Bowling Comment"

“I made you this compilation of my thoughts and feelings. The agenda for our conversation is on Page 3. Please call my office to schedule our relationship discussion.”

Dear Captain Awkward:

My boyfriend and I are in our mid-twenties and have been together for about half a year. He treats me well, takes an interest in what I do and enjoy and is generally a good boyfriend. We have a lot of similar characteristics and the same silly sense of humor. When we first got together it was supposed to be a casual thing, but it ended up escalating into something more serious almost immediately. Right now we are together almost five days of the week and almost never go out alone. We sleep in a tangled pile. We are comfortable with just being in the same room doing our own thing. I have never pressured him into anything and neither has he, everything just happened. It feels SO nice and natural. He seems to enjoy it too.

I am developing some Serious Feelings for him and I can definitely imagine a future with this man, but I am not sure about what he wants from our relationship. I would definitely want to be with someone who wants to have a family and this is not something up for compromise. My problem is that both him and I are absolutely terrible at talking about emotional things. I even have trouble saying „I like you“ out loud, asking „where do you see this relationship going“ is something I feel is beyond me. I’ve tried to find a good moment to force myself to bring up this topic with him, but can’t seem to find one (or I can’t make myself to open my mouth). I’m also afraid that he will not be able to answer my questions for the same reasons (I know I’d have trouble with it). I don’t want to lose him and yet I don’t want to waste my time in a relationship that will not lead anywhere.

So I guess my question is, how do I get over this unnatural fear I have of talking about my feelings/relationship goals? Suppose I get over it, how do I make the conversation comfortable enough for him? Do you think it’s viable if we’re both funny the same way?

Miss Wordless

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semaphore

We’ll figure this shit out.

Hi Captain & Team Awkward,

I’ve been enjoying the site for a while now and have been able to take quite a few pointers from y’all, so thanks!
 
I guess the shortest way to ask my question is this: What are the green flags in any (budding) relationship? 
 
Best wishes -
Looking Forward to More Awesomeness 

Dear Looking Forward,

Sweet Machine on deck. Thank you for giving us the opportunity to talk about good relationships instead of the icy jaws of loneliness! Instead, you’re writing from the skylight car of the Awesome Train and want to make sure you’re going the right direction. High fives all around!

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Little boy from Cinema Paradiso holding a piece of film.

You are here.

Dear Captain Awkward:

I’ve always been one for bundling, so I thought I’d bundle 3 for the price of one :) I will also try to make this as compact as possible.

#1 — I am a 19 year old guy, almost 20 in June. The first problem is that I have never kissed a girl, romantically so to speak. I have kissed a girl on the lips, but that was a dare. Now the reason for this is simple, I have not found the right girl. There have been relationships, and one in particular where I almost did kiss her, let’s call her A. But there were people all around us, and I wanted it to be special. I think the underlying issue is that I am filmmaker/musician/artist. I feel like I am the editor of my life, and I want to craft that romantic scene…those perfect moments. But in all honesty, there are very few people that I would actually date, that I know. People tell me to lower my expectations, but I simply will not. I believe there is nothing wrong in waiting for that right person. I know it happens, because it’s happened to me before. I knew the moment I saw A that she was someone I would date. And low and behold, we ended up dating. Now I understand that it is silly of me to think every moment can be that Hollywood blockbuster, and I know that now. I almost never plan things out and am a firm believer of fate. The only problem now is that I haven’t felt that initial spark with any girl I have met so far. (this will come into play with question two)

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Fred Savage in The Princess Bride. "Is this a kissing book?"

“Is this a kissing book?”

Dear Captain Awkward,

I’m in love with my best friend. That sounds like a really lackluster problem, but it’s really starting to weigh on me in a way it never has before. I’ve tried to talk to some other friends about it, but they don’t really seem to count as outside opinions (our friends are basically gunning for us to get married). I would really appreciate an unbiased viewpoint!

My best friend is wonderful in every way. We’ve been inseparable since high school. Everything we do together just seems so special and memorable, like a movie. We can keep up with each other and encourage each other. We adventure together. We can talk to each other in a comfortable stream-of-consciousness and work out our problems together. We grew up together. It’s been five years and my heart still jumps up into my chest every time he walks through the door.

I’m so in love with him, but I’m starting to wonder if anything will ever change between us. If we ever started to date, physical intimacy would be the only new development; we’ve already covered most of the bases for beginning and sustaining a healthy relationship. I’ve reached a level of intimacy with him that I’ve never found with anyone else. Pursuing a relationship with him seems so strange to me. It’s something I thought about a lot when we were a bit younger, but now it just seems silly. I see us staying friends forever, and I could even picture us being married, but I could never see us in a relationship together. It’s just been too long- it almost seems like we’ve passed the mark. I just don’t see anything to be gained by dating each other.

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