Guy’s Guide to Romancing a Lolita

September 26, 2009 at 11:20 pm | Posted in Life, Lumpy | 8 Comments
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Who knows how you meet her. Maybe she commutes on the same train as you. Maybe you see her walking around your neighborhood, or she’s a customer at your workplace. Maybe she sits in front of you in class. No matter where you found her, your mind is captured &your heart flutters when you think about her – her curls, her bows &lace, her long bejeweled lashes all make your breath come fast.

She’s unlike anything you’ve ever seen or experienced, and because of this you have no idea how to approach her. What if she’s too shy to say something to you? Ah, this old song and dance – so familiar yet this time it feels so different! Don’t worry, I know how you feel.

So you’re hooked on a lolita. It’s happened before and will happen again, to many guys &many girls around the world – intoxicated by the beauty of the poof. Your first task in pursuing her is definition. First, I’m going to start: the girl I’m talking about in this article has strong lifestyle leanings. Lolita isn’t just a weekend hobby for her; it forms a large part of her aesthetic &maybe even morals or ideals. The “you” is the pursuer. Male or female is unimportant, however I will be making the assumption that “you” are male – sorry ladies. I will also assume that “you” know only a very little bit about lolita, but are willing to learn &plan on doing your research. Now, your turn. You need to figure out what it is you like about her. If it’s just that you like how she dresses, a little warning bell should go off: if you just like her because she stands out, or if you’re sexually attracted to the style, I’m worried. You should be approaching her as a person, not just a lolita. However, appreciating the childlike innocence of her clothing or the creativity she puts into her appearance is not a bad starting point, because you can tell a lot about a person from her appearance. However, your first step in all of this is remembering that your beloved lolita is, first and foremost, a person, &you can’t know everything about someone just from the clothing he or she decides to wear.

So, you’ve examined your feelings &determined that they aren’t just flights of sexual fancy or anything otherwise detrimental to the object of your affections. Great! Now you can start wooing her. Like I said above, a lolita is a regular girl too, so anything that will work with other girls probably will work on her too – take her to the movies, or coffee, or out for drinks if you’re of age. Not every girl will go for this, however; if you really want to let your lifestyle lolita know that you’re savvy (&you better be! Do your research!), you’ll need to get a bit more creative – though admittedly, as some of these require knowing what she’s into or are a bit more sappy than others, not all of these would make a great first date.

Some of my personal favorite date ideas:

  • Of course, tea at a teahouse. You can find some great ones as well as reviews online.
  • Antiquing! You’re a real catch if you’ll put up with this for her. You have to know the right shops, though – obviously a high school girl won’t have much use for a store specializing in furniture, etc. Somewhere specializing in clothes &trinkets is good. You’ll have to do your own exploring and asking around for this.
  • Have a camera? Interested in photography? You just earned major bonus points with most lolitas. Propose a photoshoot at a Gothic cathedral-style church, forest, or graveyard – you’ll have to do some stealthy research to figure out which would suit her fancy most, which will earn you even more bonus points.
  • Go out for ice cream in a park with a pond. Skip stones, wish on pennies, and pick a bunch of dandelions for her.
  • Go ghost-hunting! Obviously this won’t be everyone’s cup of tea, but almost all the lolitas I know have a huge thing for ghosts, &there’s definitely something romantic about traipsing through a centuries-old graveyard with a digital camera. Who knows, maybe you’ll be possessed by the ghosts of a pair of star-crossed lovers! Be still my heart.
  • Find an orchard or berry farm and pick your own fruit.
  • Alternately, in winter, go ice skating with a picnic of soup, grilled cheese, &hot cocoa.
  • Look into museums. Most lolitas have a great love of or at least interest in history, and would be pleasantly surprised if they were invited to an exhibit on Victorian fashion or the history of tea. Again, stealthy research to figure out what type of exhibit would suit her fancy.
  • Take her to costume party. Wear boystyle, ouji, dandy, or even steampunk. It’d be a good way to introduce her to your friends without her feeling out of place, &if you pull off your outfit well you will have mucho brownie points, promise.

I’ve noticed most of these have a heavy gothic/classic leaning. If your girl is more interested in sweet (meaning she wears lots of light colors &childish-themed prints. Didn’t you do that research?!), try:

  • Taking her to an artisan chocolate shop…
  • …or really any candy store &buy her a pound of anything she wants. Be careful of the oncoming sugar high.
  • Take a cake-decorating class together – you’re going to have to be pretty secure in your masculinity for this, but you’ll definitely get some bonus points.
  • Go to a carnival or country fair – or, if none are available, you can go for a standard amusement park. Points for wooden rollercoasters, vintage ferris wheels, and old-fashioned carousels.
  • Find a forest or open field with wildflowers in it. Go crazy picking the prettiest blooms (not too many, please!) &make her a bouquet. As if you’re not emasculated enough as is, braid flowers into her hair. Okay, so maybe this would suit some of our lolita-hunting ladies better than gentlemen, but it’s definitely super-squishy-romantic if you can bring yourself to do it!

As I said above, note that these are not necessarily first-date material. I recommend taking your lolita out for coffee or lunch first, get to know her (stealthy research can hereby commence – make mental note of anything she says that could be used as future-date fodder), and then suggest or imply one of the above. “Oh, you’re into the paranormal? There’s a cemetary that’s supposed to be super haunted a few towns over, I’ve always wanted to go ghost-hunting there,” or, “There’s going to be a fair in town by the beach next week – ferris wheel, cotton candy, whole nine yards. I used to love going there when I was little, but none of my friends are into that stuff anymore &it’s kind of boring to go alone…” Hopefully she’ll get the hint &invite you. If not, don’t be afraid to ask her yourself! Just like any girl, some lolitas are too shy to ask themselves, or don’t want to seem too forward.

As a general tip: most lolitas are very detail- and appearance-oriented (obviously), so if you’re a bit scruffy or ill-kempt it may not be a bad idea to clean up a bit. Not saying you have to start wearing suits &go around saying “my lady,” but shaving that neckbeard or wearing a nicer shirt wouldn’t be a bad idea. Not implying that all guys are gross, but if you tend to err on the side of messy you should try and put in the extra effort – if you alreadycomb your hair &deodorize often pay this section no mind 🙂

Okay, so we’ve gone over preliminaries, dates, and appearance. All the rest is up to you – what, you want me to talk to you for her too or something?! Well, I guess you’re right, it can be kind of intimidating, and there are definitely some no-no’s that are pretty common but decidedly vexing for lolitas or, really, followers of any alternative fashion. Asking her about her clothing is never a bad idea, however realize that most of the time lolitas are on guard when it comes to their style as they usually get a lot of flack for it. Be respectful, and avoid asking her why she’s dressed “like that” or asking about her “costume” – horror of all horrors! Maybe a “I really like your dress – something special going on, or is that just your style?” or asking for details on specific pieces, but remember that too much interest can be pretty daunting or, unfortunately, in our society, may make her question your sexuality. Ask more about the detail behind the style – where did she buy her pieces? Is there a big following in your city/state/country? How did she learn about it? This will show her you’re interested in the girl inside the dress, not just the dress itself, which is important – most people see only the clothes when looking at a lolita. She’ll appreciate being seen as the person behind them for once.

Of course, as with any girl, take your cues from her. If she looks uncomfortable or is fiddling with her pencil or cellphone, she’s not happy with the conversation – best to quit while you’re ahead &maybe continue the next day or a few hours later. If she suddenly asks when the last homework assignment is due or what time the deli next door closes, you’re probably making her uncomfortable – danger, Will Robinson! Avert conversation. As with the pursuit of any mate, play it by ear &play off of her reactions. Make note of her body language and reactions, and, when talking to any object of interest, let your personalty shine &get to know her. Maybe something will happen, maybe it won’t – at least you’ll never have to say “what if?”

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8 Comments »

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  1. haha anyone who buys me candy as a date must love the sugar high, or get sugar high with me. It’ll be like an acid trip together :3

  2. I love this! I think both Date set ideas are wonderful and would have fun doing any of them.

  3. God love my boy, he met me in my pre-lolita years.
    I was the comicbook nerd, he: the comicbook vendor.
    A while ago I learned that my style made him uncomfortable at first, but he held my hand in public regardless.
    He makes me tea in my “Meow” mug, I have his back in Halo. He may wear naught but work t-shirts and scruffy combat trousers, but I wouldn’t swap him for a dandy, even if someone were to hold a gun to my head.

    • Same here! Well, he’s not uncomfortable with my lolita-ness (on contrary encourages me to be myself) but he is far from the dandy type. He’s quite geeky, into videogames, has a job as a programmer… Wears combat trousers and black shirts. He has a stubbly face but I love him like that!

      I couldn’t ask for someone better, we’re perfect for each other!

      I would like him to take me out more often, even if it’s nothing much. Heck, we’re in England, land of the tea shops… It’s the least he could do but then again, I’m shy to ask him.

  4. I really enjoyed reading your post. 🙂 I hope there will be some guys learning a bit from that.

  5. Very useful post. I think the comment on not wanting to ask about her “costume” is useful in particular. As with any hobby that stands out, lolitas are bound to be asked a lot of not-so-objective questions about why they appear the way they do, and for a gentleman who’s genuinely curious, it’s all-too-easy to bluntly ask in the same manner x(

    • Thank you! I wanted to be sure i pointed out the costume bit specifically, because it’s such a huge insult in our community but not something an outsider would guess. I’m sure many lolita-romancers have gone awry in this area!

  6. This is too cute! I don’t get to wear lolita very often, but a lot of these things definitely carry my interests. ❤ I am a lolita at heart, but not enough money to have a full wardrobe. D:


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