In this episode, Jessica and Brandon dive into a tricky but essential question: How soon should you bring up money when you're dating?

They unpack why money often feels taboo, share tips to start the conversation without tension, and explore real‐life stories about financial expectations, backgrounds, and values. Whether you're in your 20s, 30s, or beyond, you’ll get tools to help you be curious, open, and intentional in your relationships.

What You’ll Learn:

• How early is “too early” vs. “too late” to talk about things like debt, financial goals, and spending styles.
• Simple conversation starters that don’t feel intimidating.
• How upbringing & past financial habits influence what you expect (and need) in a partner.
• What to do if your partner resists having the money talk.

Questions we answer:

• Should you ask about money on date one, date two, or after you get more serious?
• What clues about a person’s financial mindset can you pick up in subtle ways?
• When is it okay to split bills 50/50 vs. proportionally?

If you’ve navigated this conversation well, or struggled badly, share your stories with us! We love hearing what works (and what doesn’t) in real life.        

Head over to our YouTube channel to catch this episode in full video form.

Apply to be a guest on the show.

You can also email us at: [email protected]

Connect with us on Instagram
We’re most active over at @thesugardaddypodcast

Chat with Brandon
Want to work together? Learn more about Brandon

Book a free 30-min call to see if it's a fit.

Show us some love, hit subscribe, leave a five star rating, and drop a quick review!

Head over to our YouTube channel to catch this episode in full video form.

Apply to be a guest on the show.

You can also email us at: [email protected]

Connect with us on Instagram
We’re most active over at @thesugardaddypodcast

Chat with Brandon
Want to work together? Learn more about Brandon

Book a free 30-min call to see if it's a fit.

Show us some love, hit subscribe, leave a five star rating, and drop a quick review!

Money, relationships, and the mindset to master both. Hosted by financial advisor Brandon and his wife Jessica, The Sugar Daddy Podcast breaks down how to build wealth, unpack old money beliefs, and have real conversations about love and finances. Our mission? To help couples and individuals grow rich in every sense of the word: emotionally, relationally and financially.