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You are currently viewing Ask Anna: How to kiss a girl for the first time (and like it). Plus, is it unusual to bring a gift on a first date?
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Ask Anna: How to kiss a girl for the first time (and like it). Plus, is it unusual to bring a gift on a first date?

This column originally appeared on the Chicago Tribune.

I’m a 19-year-old bisexual who recently started dating a girl I met online. She’s the first woman I’ve ever been with. Before her, I’ve only been on a few dates with a total of four guys, and had one long-term relationship (2 years) in high school. I’m really enjoying the time we spend together. However, I’m unsure about how to approach physical intimacy in this new relationship, as I’ve never kissed a girl before and I’m eager to do so. In my previous experiences, I’ve always waited for the other person to initiate the first kiss, and I’ve only ever kissed two people. I struggle with anxiety and social situations, which makes it difficult for me to take the first step. On top of that, she seems to be quite introverted as well, so I’m not sure if she’ll be the one to initiate either. I’m afraid of making a move and facing potential rejection. What should I do in this situation?—Kind Introvert Seeks Support

Dear KISS,

Navigating new relationships can be both exciting and nerve-wracking, especially when it comes to physical intimacy. It’s totally normal to feel a bit anxious about taking that first step, especially if you’ve never kissed a girl before.

Before we get into actual kissin’ advice, let’s get one thing out of the way first. Rejection can be a daunting prospect, but it’s important to remember that without taking risks, we’d miss out on so many worthwhile experiences in life—including the chance to kiss pretty girls. Plus, rejection is totally normal and the more we experience it, the easier it gets. Not that it’s ever fun per se (it’s not) but with time and practice, we learn that it’s not a big deal. More like a scrape. The world is enormous and not everyone wants to kiss us back, but it’s okay because there are also plenty of people who want to kiss you that you won’t want to kiss back. It goes both ways. 

My first girl kiss took approximately seven hours—because I needed all that time to talk myself into it, even though we drove hours to see each other for this express purpose. It was nearly dawn before I finally FINALLY worked up the courage to kiss her.

But when I did?

When I took that leap of faith?

Everything changed for the better. And I promptly fell into a space where I no longer had to justify my life.

Embracing vulnerability and stepping out of our comfort zones can lead to the most profound connections and unforgettable moments. So, take a deep breath and muster up the courage, because sometimes the sweetest rewards come from facing our fears head-on. After all, you never know what magic awaits on the other side of that first kiss. 

Now onto the tactics. Since both of you are introverted, it might take a little extra effort to break the ice. Here’s an idea: why not try to create a comfortable and cozy atmosphere during your next date? Pick a relaxed setting, like watching a movie together or going for a walk in a quiet park. This can help set the stage for a more intimate moment.

When the time feels right, you can gently bring up the topic of physical affection. Don’t underestimate the outright ask—“I’d really like to kiss you. Can I?”—works wonders if you’re unsure. (Plus, consent is sexy.) You can also share your thoughts and feelings with her beforehand, and let her know that you’re eager to kiss her, but you’re also a bit nervous about making the first move. Honesty and vulnerability are super hot, and it can help build trust between the two of you.

Chances are, she might be feeling the same way. By opening up about your desires, you give her the opportunity to share her own thoughts and preferences. This can pave the way for a more natural and comfortable first kiss.

Remember, with queer dating, there’s no strict rule on who should initiate the first kiss. The most important thing is to communicate openly, respect each other’s boundaries, and take things at a pace that feels right for both of you. 

Good luck, KISS.

I’m a 25-year-old guy who’s finally meeting a guy I’m really into after chatting on Hinge for a while. We’re meeting at his place. I’m curious, do guys nowadays bring gifts on first dates? If so, what would be a thoughtful and appropriate gift? One idea I had was to grab a small cake from my workplace (since it’s free for us employees, haha) and bring it over to his place.—Getting Into the First Time

Dear GIFT,

It’s not super common to bring gifts on first dates (anymore, though the Victorians loved that shit). That said, when I met my wife—oh hey, I got married this weekend—whom I had been talking to for five weeks online (because pandemic), I brought an excessive amount of gifts to our first date (homemade strawberry shortcake, flowers, Totino’s party rolls, etcetera).

So! While it’s not common to bring a gift, if it fits your vibe and style, then I say go for it. Plus, who doesn’t love free cake? And if said cake is a work perk, then it’s a pretty small gesture, so not that out of the ordinary. 

And, if we’re being all etiquette-y, it’s also not uncommon to bring a small gift to the host of, say, a party, which your guy technically is, though he’s only hosting a party of two. A beverage is a nice touch, like a bottle of wine or a premade cocktail. 

TL:DR; it’s not necessary to bring a gift, but under the right circumstances and vibe, it’s a small, thoughtful token.

PS: If this is a sex date, then all you need to bring is protection and a game attitude.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books

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