Ranking Every *Mindy Project* Boyfriend: From Worst to Best (With Deep Analysis)

Oh, Dennis. The human equivalent of a LinkedIn humblebrag. Played by Glenn Howerton (yes, It’s Always Sunny’s Dennis Reynolds), this corporate lawyer was Mindy’s Season 1 attempt at dating a "grown-up." Spoiler: It went as well as you’d expect.

Why He’s the Worst:

• Zero Self-Awareness: His "I’m a lawyer, baby" pickup line wasn’t just cringe—it was a lifestyle. He genuinely believed his own hype, from his "elite" gym membership to his insistence that Mindy should be grateful for his attention.
• Emotional Stuntedness: When Mindy tried to break up with him, he responded with "You’re dumping me? That’s so brave." The man couldn’t even muster basic human emotion.
• No Chemistry: Their dates felt like a hostage negotiation. Remember the scene where he took her to a steakhouse where he knew the chef and then spent the whole time name-dropping? Mindy’s deadpan "This is the worst date ever" was the audience’s exact thought.

Red Flag Moment:

The nail in the coffin? When he recorded their breakup to "analyze it later" for self-improvement. Not only is that psychopathic, but it also proves he saw Mindy as a project, not a person.

Could It Have Worked?

No. Dennis was a plot device to show how far Mindy had to go in terms of self-worth. The fact that she dated him at all is a testament to her early-season desperation to be "the cool girlfriend."

9. Cliff (The "I’m Too Good for You" Hipster)

Played by Max Greenfield (pre-New Girl fame), Cliff was the smug, bike-riding, artisanal-pickle-making hipster who made Mindy feel "not cool enough." Their relationship was a masterclass in how insecurity fuels bad decisions.

Why He’s Terrible:

• Condescension as Foreplay: Cliff’s entire personality was "I’m better than you, but I’ll date you anyway." He shamed Mindy for liking mainstream things (like Sex and the City) while acting like his obscure tastes made him superior.
• Passive-Aggressive Breakup: Instead of dumping her, he ghosted her via a mix CD with songs like "You’re So Vain." That’s not quirky—that’s emotionally immature.
• No Accountability: When Mindy called him out, he played the victim: "You’re too sensitive. It was just a joke." Classic gaslighting.

Key Scene Breakdown:

Their breakup in "Josh and Mindy’s Christmas Party" (S1E11) is a gut-punch. Mindy, dressed in a ridiculous elf costume (because Cliff demanded it), realizes he’s ashamed of her. His "You’re just not my type" is the ultimate mic drop—he never saw her as an equal.

What It Revealed About Mindy:

This relationship exposed Mindy’s tendency to shrink herself for men. She pretended to like indie bands, wore his weird clothes, and even changed her laugh to seem cooler. Cliff was the wake-up call she needed to stop performing for love.

8. Glenn (The "I’m a Priest" Curveball)

Yes, Mindy dated a priest. Played by Stephen Tobolowsky, Father Glenn was a Season 2 wild card—a man of God who also happened to be hilariously human. Their fling was short but iconic.

Why He’s Low on the List:

• Obvious Dealbreaker: He’s a priest. Even if he left the clergy (which he considered), the power imbalance and moral dilemma made this DOA.
• No Real Stakes: Their relationship was more of a comedic bit than a serious arc. The show treated it like a "what if?" rather than a real possibility.
• Mindy’s Ego Trip: She loved the idea of being "the woman who tempted a priest," not Glenn himself. It was all about the story, not the connection.

Best Moment:

Their first kiss in the church (“I’ve never done this before”) was surprisingly sweet—until Mindy immediately started bragging to her friends. Classic Mindy: turning sacred moments into social capital.

Could It Have Worked?

No. But it was a brilliant satire of Mindy’s tendency to chase ideas of men rather than actual compatibility. Also, the show nailed the absurdity of dating a priest (e.g., him blessing her apartment before sex).

7. Jody (The "I’m a Teenager" Mistake)

Jody Kimball-Kinney (played by Garret Dillahunt) was the Season 3 fling who looked like a grown man but had the emotional range of a 16-year-old. Their relationship was a hot mess—literally and figuratively.

Why He’s Flawed:

• Peter Pan Syndrome: Jody lived in a loft with a slide, threw tantrums when he didn’t get his way, and had a "no rules" philosophy that extended to monogamy.
• Mindy’s Regression: Instead of calling him out, she joined him. Remember the episode where they trashed a hotel room? She became as immature as he was.
• Zero Future Potential: He didn’t want kids, a stable job, or even a real relationship. Mindy ignored all of this because the sex was good.

Most Cringe-Worthy Moment:

Their breakup, where Jody cried "You’re breaking up with me because I’m too fun?!" while Mindy realized she’d wasted months on a man-child. The show framed it as her "growing up," but it was also a critique of how women excuse bad behavior for excitement.

What It Taught Mindy:

That chemistry isn’t enough. Jody was the first time Mindy admitted she wanted more—stability, respect, a partner who didn’t make her feel like his mom. It was a turning point.

6. Ben (The "Almost Perfect" Ex)

Ben (played by B.J. Novak) was Mindy’s college boyfriend who reappeared in Season 4 as a very successful app developer. Their reunion was electric, but ultimately, he was a reminder of why exes are exes.

Why He’s Mid-Tier:

• Unresolved Baggage: Their breakup in college was messy (he cheated; she never fully trusted him again). Rekindling that was always risky.
• Power Imbalance: Ben was rich, powerful, and had moved on emotionally. Mindy was still figuring herself out. Their dynamic felt uneven.
• Timing Was Off: They got back together right as Mindy was finally becoming her best self. Ben was a distraction from her growth.

Best Scene:

Their first reunion in "While I Was Sleeping" (S4E1) is one of the show’s best cold opens. Ben walks into her office, and the tension is palpable. Their banter (“You look exactly the same” / “So do you. Like a hot nerd”) is peak Mindy/B.J. Novak chemistry.

Why It Didn’t Last:

Ben represented Mindy’s past—the girl who settled, who ignored red flags. By Season 4, she deserved better. Their breakup (where he admitted he still loved her but couldn’t commit) was heartbreaking but necessary.

5. Leo (The "Too Good to Be True" Fling)

Leo (played by Anders Holm) was the Season 5 love interest who seemed perfect on paper: handsome, successful, actually into Mindy. So why isn’t he higher on the list?

Why He’s Underrated:

• Healthy Dynamics: Unlike most of Mindy’s boyfriends, Leo listened to her. He supported her career, respected her boundaries, and—gasp—communicated.
• Mindy’s Growth: With Leo, she wasn’t performing or chasing. She was just… happy. No games, no drama.
• Realistic Conflict: Their breakup wasn’t about toxicity—it was about timing. Leo wanted kids; Mindy wasn’t sure. That’s a valid, adult reason to part ways.

Why He’s Not #1:

Because the show didn’t give him enough screen time. Leo felt like a reaction to Danny—a way to prove Mindy could have a normal relationship. But the lack of passion (compared to her and Danny’s fireworks) made it feel flat.

Key Quote:

Leo: "You’re amazing, Mindy. But I can’t wait forever for you to figure out what you want." Ouch. But fair.

4. Josh (The "What If?" Romance)

Josh Daniels (played by Tommy Dewey) was the Season 1–2 love interest who almost worked. A fellow doctor with a heart of gold, Josh was the first man who made Mindy consider settling down—for about five minutes.

Why He’s Great:

• Genuine Kindness: Josh was sweet, stable, and actually liked Mindy for who she was. No games, no ego.
• Shared Values: They were both doctors, both family-oriented, and both wanted similar things (eventually).
• Mindy’s Fear: Their breakup wasn’t about him—it was about her fear of commitment. She self-sabotaged because she wasn’t ready.

Why He’s Not Higher:

Because the show never fully committed to him. Josh was always the "safe" option, the guy Mindy should want—but the audience (and Mindy) were waiting for someone with more spark.

Best Episode:

"Josh and Mindy’s Christmas Party" (S1E11) is a masterpiece. Their almost-kiss under the mistletoe, ruined by Mindy’s panic, is one of the show’s most realistic moments about fear and timing.

Could It Have Worked?

Yes—but only if Mindy had been in a different place emotionally. Josh deserved someone who chose him without hesitation.

3. Morgan (The "Unexpected Soulmate" Wildcard)

Yes, that Morgan. Mindy’s ex-con, germaphobe, oddball best friend (played by Ike Barinholtz) wasn’t just comic relief—he was her platonic soulmate. And in Season 6, they almost crossed the line.

Why He’s Iconic:

• Unconditional Love: Morgan loved Mindy exactly as she was—flaws, ego, and all. No one else on the show accepted her so fully.
• Chemistry: Their friendship had more spark than most of her romances. Remember their fake marriage in "Mindy and Danny’s Wedding"? Pure gold.
• Missed Opportunity: The show teased a Morgan/Mindy romance in the finale, and fans lost it. It would’ve been messy, weird, and perfect.

Why They Didn’t Date:

The show played it safe