8 Ways Authentically Nice Guys Can Finally Start Finishing First

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Man with his dog

My client, Blaine, had enough of being dumped and hearing, "We don’t have chemistry" or "I love you, but I am not in love with you",  and "it’s not you, it’s me." He couldn’t understand why relationships that started well could nose dive after a few dates, why a woman could go from hot to cold. Why they didn't see the nice guy he was, the person who had so much to offer?

He was a good-looking guy, supportive and kind. During our sessions, Blaine's frustration was palpable. His body language spoke volumes—slumped shoulders, furrowed brows, and a noticeable lack of enthusiasm. It became clear that he was in desperate need of answers.

Upon closer examination, I identified several factors contributing to Blaine's dating woes. Like many, he had fallen prey to three common misconceptions.

Three common "myths" of dating as a genuinely nice guy:

  • The Myth of Niceness: Believing that being a nice guy automatically guarantees attraction.
  • The Trap of Transactional Expectations: Believing that meeting a partner's needs guarantees reciprocation.
  • Illusions of Perfection: Expecting life to be smooth sailing if he followed all the "right" steps.

However, as Dr. Robert Glover insightfully points out in his book, No More Mr. Nice Guy, genuine attraction isn't sparked by a people-pleasing guy seeking external validation. Moreover, the women who stick around hungry for love won’t stay when the support cup is full. By then, they may have seen the negative underbelly of a people pleaser.

My client, Blaine, admitted how resentful and angry he was after these unfulfilling dates. He described a growing and depressing streak of meanness, wavering between niceness, cruelty, and rage that broke his own coffee table (when he was alone, not when a partner was around) and screamed at cars in traffic. He was ready for a reboot.

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Here's how authentically nice guys can start finishing first (and still be themselves).

1. Rediscover yourself.

I encouraged Blaine to press pause on dating and reconnect with his interests. It was hard to convince someone who didn't like or know himself to spend time alone, but in a few weeks, Blaine was tinkering with his car, hiking the woods, and renewing a relationship with the person he was when happiest.

2. Embrace authenticity

Encouraging authenticity required discussion and homework. In this period, Blaine learned that authenticity goes beyond mere honesty into understanding and expressing one's core values and needs. He understood that complimenting a girl on her appearance doesn't require him to like the color and style of her dress but to say what he did like. Blaine began to communicate his thoughts and preferences genuinely, without fear of judgment.



3. Set healthy boundaries.

Our conversations revealed Blaine as a “yes-man” who had spent years at work and home flying under the radar, with his talent and skills overlooked because he was “invisible.” He recounted an incident where the waiter forgot his side order and served the food cold, and he didn't complain. This happened on a third date with someone he believed was the one. The chemistry was great, their laughter bubbled, and she had the works but left with the words, It’s not you, it’s me which I translated as “You won’t stand up for me if you don’t stand up for yourself.”

Already In his late thirties, Blaine had never heard the word boundaries applied to a healthy relationship. so our discussion led to his purchase of the foundational book by Henry Cloud and John Townsend. Learning to express his needs and preferences was a crucial step toward reclaiming his self-worth.

Let me pause to say not all nice guys are boundaryless, inauthentic, resentful, and rageful to the extent Blaine had become. Some nice guys have limits to what they tolerate and are balanced in their desire for a relationship. Some even have committed relationships with those who value their supportive nature. But if you suspect your significant other has anything less than the highest regard for you, begin to make changes inside and out.

Ask, “ Am I trying too hard? Am I too worried about another’s opinion and hungry for approval?” Ask yourself, Is my niceness and desire to please a reaction to feeling unlovable, defective, or unworthy?

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4. Address your shame.

With moist eyes, Blaine recalled his early years of being punished with silence, overlooked when he longed for praise and told to “man up” his emotions and vulnerability. Helpless to gain acceptance and value, he learned to shelter his feelings and fly under the radar. He admitted he alternated from feeling like an imposter and anxious he would be discovered as unworthy to secretly hoping to meet someone who believed he was worthwhile.

Blaine's shame explained why he would control and manipulate situations, withhold negative self-disclosure, and defend and excuse everything. In the non-judgemental setting of the therapy office, Blaine began to heal and became more aware of when and how he drifted into old patterns. Awareness combined with self-understanding and curiosity helped him more than he expected. But the real challenge was learning a non-defensive approach.

5. Seek positive support.

The advice to join a men’s group was borrowed from Dr Glover’s book, and it helped Blaine relax and connect without emotional tension. He didn't stop there but embraced prioritizing all relationships, where he could give and receive equally. Soon, Blaine reconnected with college friends and planned a Super Bowl party where everyone arrived with a six-pack, wings, and chips.

When Blaine was ready to date, he had a new appreciation of who he was. He had the innate traits of stability, moral integrity, respect, and kindness women want. He had also learned to be lighthearted and the tiniest bit of a bad boy.

happy man at support group

Photo: LightField Studios via Shutterstock

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6. Embrace lightness.

As a more conscious and aware guy, Blaine appreciated his flaws, anxieties, and shortcomings as never before and adopted a healthy balance between his needs and hers. It wasn’t just his updated haircut and wardrobe spelled change. It was also his decluttered apartment, desk, and worn-out friendships. Blaine was almost ready for the dating pool and I encouraged speed dating so he could display his rogueish side.

7. Create fun tension.

“Nice” does not inspire the emotional tension needed for attraction and arousal. If she isn't a little uncertain about how you feel, she will move on, and you will be relegated to the friend category. On the other hand, if she wonders, He loves me, he loves me not, her heart beats faster, and she interprets attraction as love.

The “Love Bridge” tells the story of physical attraction in an environment of heightened anxiety versus a tame and calm setting. Conducted by Dutton and Aron in 1973, this research placed an attractive woman on a route that interrupted nervous men crossing a swaying bridge with low handrails and a 230-foot drop to the river below. The same attractive woman also intercepted men crossing a significantly safer bridge. The woman invited all the men to call her after crossing the bridge.

Markedly more men who crossed the scary bridge telephoned the woman. Dutton and Aron interpreted that fear had been transformed into attraction. My suggestion to Blaine was to have “scary” fun with his dates, adding roller coaster rides and out-of-town adventures to the more peaceful riverbank picnics.

8. Embrace your authenticity.

In the end, Blaine discovered that true fulfillment in relationships comes from embracing one's authenticity. By prioritizing self-discovery, setting boundaries, and fostering genuine connections, he transformed himself into a catch—a confident, emotionally intelligent individual who was proud to share his life with others.

So, if you find yourself stuck in a cycle of unfulfilling relationships, remember: focus on your happiness and not people pleasing. This begins with embracing your true self and not a well-modified or “nice” version.

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Reta Faye Walker is a therapist who specializes in healing relationships. She offers one-on-one sessions, couples retreats, and courses to help couples get back on track.