Date Everything! Guide | How To Romance Penelope

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

Game Guide by Ragib Rawnak on Jul 07, 2025

Successfully romancing Penelope requires patience, persistence, and strategic dialogue choices throughout her series of failed dates with other Dateviators in Date Everything!

Penelope represents office stationery within the game's unique dating mechanics, and pursuing her involves witnessing her romantic failures while consistently positioning yourself as the superior alternative.

This guide will aid you through each encounter, providing the optimal dialogue choices to build romantic tension and ultimately win her affection after she experiences disappointment with multiple other potential partners in Date Everything!

Date Everything Guide, How To Romance Penelope

Initial Meeting and First Impressions

To begin your relationship with Penelope, you must use your Dateviators on office stationery items. Target the large pinboard located in the Office area, as it provides the easiest interaction opportunity.

Upon successful activation, you'll immediately receive a collectible when Penelope appears and shows you a magazine titled "Office Romance."

Initiate the conversation by asking Penelope about the publication with the dialogue option "Office Romance Magazine?"

This allows her to introduce herself properly and establish the foundation for your ongoing interactions. She'll comment that you haven't utilised her services recently, so select any dialogue option except the third choice to maintain positive momentum.

Penelope will mention that your presence is beneficial because you can serve as a witness to her "resurrection." Interrupt her mid-sentence by asking, "To what?" to show engagement in her explanation.

After she clarifies that she isn't deceased, you have two romantic options: either flirt with "You're too cute to be single" or provide encouragement with "You're so right, queen."

Setting Up Her Dating Journey

Penelope will then recite a quote from "Stephen Stovey" about her most significant work lying ahead rather than behind. If you're pursuing romance, respond with "Lead with your best asset - dat ass" to make her blush and establish your playful, flirtatious tone.

She'll reveal her plans for a "very hot date with a cross-trainer" and seek your advice. Provide guidance using either of the top two dialogue options to maintain a favourable opinion of you before she departs for her date with Kristof in Date Everything!

Date Everything Guide, How To Romance Penelope

Second Encounter: The Shelley Disaster

Your second meeting begins with Penelope sharing another quote, this time attributed to "Marker Twain." Ask her, "Another 'Quote of the Day'?" to acknowledge her pattern of inspirational quotations.

She'll confess that her previous date was catastrophic, so encourage her to elaborate by selecting "Tell me about it..." Penelope will explain that Kristof transformed their romantic encounter into a training session, completely missing the point of dating.

Despite this setback, Penelope remains optimistic about her next scheduled date. Seize this opportunity to position yourself as a better alternative by telling her, "You should date me instead," which will cause her to blush.

She'll treat your suggestion as playful banter before requesting advice about whether she should present herself as feminine or masculine. Respond with "Feminine and fine? Sounds like you're describing yourself" to deliver another compliment while answering her question.

Shelly the Shelf will arrive during this conversation, causing Penelope to panic about the impending date. Support her by saying, "I'd be excited about dating Penelope, too," which will make her blush once again before the pair leaves together.

Third Encounter: Chance's Randomness

Penelope begins your third meeting by hinting at another dating failure through a quote from Aristotle" Respond with "Aristotle really knew his sh*t" to acknowledge her philosophical reference.

She'll describe how Shelly cried throughout their entire date, saying terrible things, which created an uncomfortable situation.

Express disbelief at Shelley's behaviour by saying, "She had a babe like you on a date and cried the whole time?" to simultaneously flirt with Penelope and criticise her date's poor conduct.

Penelope will dismiss the previous failure, claiming she's found another date who genuinely attracts her. Seize this moment to suggest yourself as an alternative with "If that's all it takes, I'm around... and alive too," which will make her blush despite her attempts to deflect your advances in Date Everything!

Chance will appear during this conversation. Question his approach by asking, "Are you dating or LARPing?" when he and Penelope provide contradictory information about their plans. Chance will recover from his initial awkwardness, and both will leave together for their date.

Date Everything Guide, How To Romance Penelope

Fourth Encounter: Skylar's Rejection

Your fourth meeting follows the established pattern: Penelope reports another dating disaster before mentioning her subsequent planned encounter.

Take a more direct approach by asking, "Are you finally ready to give up and date me?" to make her blush while highlighting the pattern of failed relationships in Date Everything!!

Penelope will recount how Chance left everything to random fate, even refusing to see her again after rolling a low number on his dice.

Continue your romantic pursuit by declaring, "You deserve better... you deserve me," to emphasise your consistent availability and genuine interest. She'll reject your advances just as Skylar arrives for their scheduled date.

The Datevians won't express much enthusiasm about Penelope, so they warn her by saying, "Oh, you're about to get dumped", which proves prophetic. Skylar will immediately reject Penelope because she wears glasses, creating an absurd situation.

Point out the logical inconsistency with "But you are glasses..." and when Skylar attempts to justify her position with a comparison about liking other humans, respond with "That doesn't make any sense!" Skylar will leave without Penelope, abandoning her completely.

Offer comfort in this moment of rejection by asking, "Would you like a hug?"

Penelope will reject your offer and go back to the Kitchen, closing out this meeting on a sad note in Date Everything!

Final Encounter: Winning Her Heart

Penelope's attitude in your final meeting will differ significantly, as she approaches with a negative perspective on people getting what they deserve rather than what they want.

Counter her negativity with enthusiastic support by declaring, "NO! You deserve the best!" to show your belief in her worth.

Sinclair, the sinner, will appear and attempt to court Penelope during this conversation. Challenge her directly by asking, "Are you really gonna date this guy instead of me?"

This final confrontation will prompt Penelope to confess her feelings with the declaration, "I APPRECIATE YOU... LIKE, ROMANTICALLY!"

You'll receive three response options that determine the relationship's outcome:

"Oh... can we just stay friends?" - You'll stay as friends if you choose this dialogue.

"I appreciate you too... about time you noticed." - You'll become lovers if you have chosen this dialogue.

"This is the greatest day of my life." - You'll become lovers if you have chosen this option.

Date Everything Guide, How To Romance Penelope

Select either of the love options to pursue romance, then confirm your interest by responding "I'd love to" when Penelope asks you out on a date. This completes your successful romance with Penelope after supporting her through multiple failed relationships in Date Everything!.

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