Blaine Anderson | A Dating Coach Explains Why Modern Dating Feels So Hard!

#918. Dating advice is everywhere — and somehow it’s made dating feel harder.

This week, Kaitlyn sits down with Blaine Anderson, a dating coach and matchmaker who works with thousands of men behind the scenes of modern dating. She shares what women rarely get to hear: how men experience dating, why “good guys” get overlooked, and where connections quietly fall apart.

They talk attraction, effort vs. interest, dating apps, and how to tell if a man is being intentional or just keeping his options open. With Valentine’s Day around the corner, they also get real about feeling behind, comparison, and staying open to love without settling.

If dating has you confused, burnt out, or questioning the rules — this episode will make you feel clearer, not broken.

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EPISODE HIGHLIGHTS: 

• (12:29) Why “nice guys” get overlooked.
• (17:05) The biggest shift in dating over the last 5–10 years — and why so many people feel burnt out right now.
• (45:52) How women can tell if a man is being intentional… or quietly keeping his options open.
• (55:08) The unexpected dating dealbreaker Blaine hears all the time.

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