In this podcast episode, Raif and Rahul sit down with Blaine Anderson to talk honestly about what actually works in modern dating and why so many people feel frustrated, burned out, or stuck even when they are getting matches. Blaine shares how she built Dating By Blaine from simple profile feedback into a full coaching and matchmaking platform, and why more people are looking for guidance as dating apps leave them confused about what they are doing wrong.

The conversation dives into Blaine’s focus on coaching men, how she decides who she works with, and why clarity, confidence, and intent matter more than trying to say the perfect thing or play a role. Together, they unpack why dating often feels harder than it needs to be and how small mindset shifts can make a real difference.

Things get practical as Blaine breaks down the mistakes that quietly ruin dates before they even start. From profile red flags and awkward first messages to texting habits that kill momentum, she walks through patterns she sees every day. Raif and Rahul also guide the discussion toward dating after divorce and long relationships, especially for men over 35, and how to be honest about your life without oversharing or turning early dates into therapy sessions.

The episode wraps with first date strategy and real life stories, including where to go on a first date, coffee versus drinks, and the small details that actually make someone feel comfortable. Along the way, Blaine shares unforgettable client requests and matchmaking moments that reveal what people say they want versus what actually leads to real connection. Raif and Rahul close the episode by tying dating, intention, and common sense together in a way that feels refreshingly real.

Timestamps:

02:23 Getting to know Blaine Anderson

08:05 Matchmaking Criteria and Courses

10:01 Dating as a Marketing Problem

11:11 Confidence and Intent

12:06 Reprogramming and Intentionality

12:59 First Date Do's and Don'ts

14:41 Red Flags on Dating Apps

17:38 Messaging and first impressions

18:11 Texting etiquette

20:23 Choosing the right first date

22:23 Creating the Perfect Setting

23:38 Considerate Gestures

23:41 Leftovers on First Date

25:29 Client's Oddball Demands

28:07 Criteria for Choosing a Partner

30:11 Opposites Attract

35:31 Prenup and nerdy hobbies

36:38 Last-minute prenup and undo duress

37:30 Values Conversation and Prenup Timing

38:29 Postnuptial Agreements

40:21 Unusual Matchmaking Story

42:58 Niche Interests and Online Dating

Episode Links:

Blaine Anderson is a well-known dating coach and matchmaker who specializes in helping men improve their dating lives and build long‑term relationships.​ She runs Dating By Blaine, a brand that includes coaching, online courses, matchmaking, and free online content aimed at guys. A couple months ago, Blaine launched a fun and helpful new podcast, “Help Me, I’m Single,” where she helps singles figure out how to improve their dating lives - featuring Blaine and a comedian in every episode. https://www.youtube.com/@DatingByBlaine

Handy Divorce Links:

Need a consultation for your Chicago area divorce? Click here https://bit.ly/3WvnqzR

For more information about STG Divorce Law, visit www.stglawfirm.com.

For I Just Want This Done, our bestselling guide to divorce, check out https://a.co/d/1QL4rBh

To sign up for our free biweekly Illinois divorce webinar, go here - https://go.stglaw.com/webinar

Want to join our free Illinois Divorce Support Network, our private Facebook group? Link is here -https://bit.ly/4ibJrhb

And for social media, free educational content, podcast, and more, check out: https://bit.ly/43LzbXb

As always, state law varies. This is not legal advice. Consult with a skilled divorce lawyer in your area for information about your specific situation.

The hosts kick things off with a breakdown of Nicole Kidman’s divorce settlement, followed by a discussion of Dan Gilbert’s (RocketMortgage) divorce and what high-asset cases can teach us about planning, leverage, and expectations when money is on the line.

From there, the focus shifts to broader cultural patterns, including the continued rise of “gray divorces” and the surprising emergence of divorce rings as a new post-split status symbol. The episode also detours into the tech world to talk about a Dutch couple who used AI to write their wedding vows with unexpected results, sparking a deeper conversation about legal tools, artificial intelligence, and the real risks of AI hallucinations when people rely too heavily on technology for legal advice.

Raif and Rahul share practical “divorce month” tips for anyone contemplating or navigating a separation, before answering listener questions on parenting plans and how courts handle future terms when spouses want different paths to resolution. The episode wraps up with a forward-looking take on dating, highlighting habits to ditch as 2026 approaches, and closes with final thoughts that tie law, relationships, and common sense together in a way only they can.

Timestamps:

09:00 Nicole Kidman's divorce settlement

14:19 Dan Gilbert's divorce

16:53 Gray Divorce Trend

18:41 Divorce Ring Trend

21:17 Dutch AI Speech Fail

22:57 Legal Tools and Hallucinations

26:43 Divorce Month Tips

34:30 Question: Parenting Plan

39:55 Question: Future Terms, Differing Resolution

43:37 Dating Habits to Ditch in 2026

46:40 Closing Remarks

Episode Links:

• Nicole Kidman Scores Big Win in Keith Urban Divorce Settlement https://bit.ly/45B6UDJ
• Oakland County judge OK's settlement agreement for Dan and Jennifer Gilbert divorce - https://bit.ly/49OEPtU
• Rocket Mortgage Founder Dan Gilbert’s Soon-To-Be Ex-Wife Is Now A Billionaire - https://bit.ly/49qwBsT
• Rachel Zoe joins 'divorce ring' trend with giant diamond after Rodger Berman split - https://bit.ly/4qqpqXL
• Dutch couple are "not married" due to ChatGPT speech fail - https://bit.ly/49sZdBS
• 5 Dating Habits to Ditch in 2026 (Before They Ruin Your Year) - https://bit.ly/4jMUGh9

Handy Divorce Links:

Need a consultation for your Chicago area divorce? Click here https://bit.ly/3WvnqzR

For more information about STG Divorce Law, visit www.stglawfirm.com.

For I Just Want This Done, our bestselling guide to divorce, check out https://a.co/d/1QL4rBh

To sign up for our free biweekly Illinois divorce webinar, go here - https://go.stglaw.com/webinar

Want to join our free Illinois Divorce Support Network, our private Facebook group? Link is here -https://bit.ly/4ibJrhb

And for social media, free educational content, podcast, and more, check out: https://bit.ly/43LzbXb

As always, state law varies. This is not legal advice. Consult with a skilled divorce lawyer in your area for information about your specific situation.