Date Everything! Guide | How To Romance Diana

Here's a guide on how to romance Diana in Date Everything!

Game Guide by TauxicPandA on Jul 07, 2025

Diana is a unique character whose storyline focuses on helping her discover her own identity while gradually separating from you. This journey of independence becomes the foundation for a romantic relationship. The entire questline requires exactly five visits to complete successfully in Date Everything!

Date Everything Guide, How To Romance Diana

Initial Encounter

Diana can be found in only one location throughout the game: she appears as a Diary with a distinctive heart-shaped cover, positioned on the drawers in the Bedroom, directly beneath the Mirror.

Your first interaction with her may seem very odd, as she tends to speak in a very confusing way. The key to romancing her is maintaining a respectful tone throughout all of her conversations, regardless of how confusing her dialogue becomes.

During this initial meeting, simply continue being polite as she jumps between various topics without any apparent logic in Date Everything!!

While she won't reveal her name during this encounter, maintaining a respectful approach will successfully unlock the interaction.

After this brief meeting, she will depart, requiring you to return on another day to continue the questline in Date Everything!

Date Everything Guide, How To Romance Diana

Building an Understanding

When you visit Diana for the second time, you'll notice she communicates more directly than during your first encounter. Upon her acknowledgement of your presence, respond with "Yeah, hey. Little nervous to be back here, but I came" to demonstrate your genuine interest in continuing the conversation.

This response will prompt her to begin dropping subtle hints about her true nature in your diary. Once she begins revealing these clues, tell her, "Think, I think we actually have a lot in common" to establish a connection.

This will trigger another episode of her characteristic rambling about seemingly random topics. When this happens, ask her to "slow down a minute", which will redirect her attention toward discussing various fears and concerns, though these aren't actually her own experiences.

The breakthrough moment comes when you say, "It was awful. I remember writing about that the night it happened." This statement will finally help Diana understand that you are her original author in Date Everything!

However, don't expect immediate celebration, as she will begin expressing disappointment about the negative memories you've recorded on her pages.

This reaction will unlock Collectible and prompt her to question why you wrote such dreadful experiences.

Respond with "I needed a friend" to acknowledge her past role in your life. While this answer may leave her feeling somewhat melancholy, she will take pride in having fulfilled her purpose during those challenging times.

When she indicates that circumstances have changed, ask, "Are you saying you'd talk about what I wrote in you?" to continue the dialogue. She will confirm this willingness while expressing some regret.

Counter her apology with "Sure it does, I can tell you're trying" to offer encouragement. This exchange will lead her to discuss methods for breaking free from her current limitations before concluding the day's interaction.

Exploring Possibilities

Begin your third visit by complimenting Diana with, "Your mind is amazing." She will likely return to her previous complaints about negative memories while simultaneously expressing her desire to develop an independent identity separate from you in Date Everything!!.

When she voices this aspiration, offer your support by saying, "Maybe we could try together." This suggestion will initially cause her to request that you leave, but don't be discouraged by this reaction.

Date Everything Guide, How To Romance Diana

Creating New Memories

Your fourth visit starts with a simple greeting to Diana. Accept her apologies by responding, "I'm sorry, too," when she expresses regret about the previous day's interaction.

When she asks for an explanation of your apology, tell her, "I didn't call. I didn't write" to acknowledge your shortcomings. This honesty will prompt her to express her need for original words and thoughts.

Offer assistance by saying, "I have an idea about how to give you your own words." When she mentions a carton during this conversation, "Which one would you like to hear?" Follow this up with "I'll own it, and then you won't have to anymore" when she begins to question herself about the choice.

Diana will then present you with various story options to help transfer ownership of memories. Select "the prettiest story" from the available choices.

She will ask you to make another selection within that category, so choose "Edinburgh, Scotland?? Cool!" This decision will unlock another collection for your collection.

As Diana begins discussing a theatrical performance, interject with "You only remember this scene because this is the moment I wrote about" to help her understand the nature of recorded versus experienced memories.

When she continues, You weren't in the wings, though. What do YOU remember?" to encourage her to access her recollections rather than your written accounts.

Encourage as she admits to waiting for you during your holiday absence, then ask, "Wait... this is your memory, right?" to help her recognise the distinction between her experiences and your documentation.

Conclude this meaningful exchange by saying, "That's amazing. Different memories, but we were so in sync." Diana will express gratitude for your assistance and request that you return for a final conversation in Date Everything!

Making the Choice

During your fifth and final visit, Diana will reveal that she has been thinking about you since your last meeting. Show interest in her thoughts by asking, "So tell me about your idea!"

She will propose a new dynamic where she serves as a trusted confidant rather than a passive diary, fundamentally changing the nature of your relationship.

When she asks, "What do you think?" you will be presented with three distinct response options that will determine the outcome:

For a Friendship route, select "I love this. I've always considered you... But now I consider you a Friend." This choice establishes a complicated but meaningful connection between you and Diana.

If you prefer to maintain distance, choose "I don't know... not really looking to talk to anyone. Sometimes, I just need to unload and forget." This option will result in a Hate relationship status.

Date Everything Guide, How To Romance Diana

To pursue the romantic storyline, select "It's a good beginning. But... being honest, I was looking for something even more... intimate." This choice will trigger additional dialogue prompts, but as long as you have maintained respectful and kind interactions throughout the previous visits and continue to be supportive during these final exchanges, Diana will agree to become your romantic partner in Date Everything!.

Also, check our Date Everything! Review and other guides below: