The Raw Reality of Dating in Your 30s as a Man: Learning from Failures and Success Stories

Written by Kentaro Sato
30代男性が婚活について考える様子

'I thought getting married would be easy once I hit my 30s' - I want to punch my 20s self who thought that. Now I'm 37. After 3 years of dating, I finally met a wonderful partner, but the journey was far more challenging than I imagined.

In this article, I'll share the harsh reality that men in their 30s face in the dating market, my numerous failures, and the practical strategies I learned from them. **No sugar-coating** - just real experiences.

The Brutal Truth of the Dating Market for Men in Their 30s

Supply and Demand Imbalance

The position of men in their 30s in the dating market is honestly tough. Statistics show that about 47% of men in their early 30s are unmarried, and 35% in their late 30s. Meanwhile, unmarried women of the same age are 34% in early 30s and 23% in late 30s.

In other words, **there's an overwhelming surplus of men**. I initially didn't know this reality and was optimistic, thinking 'I'm still in my 30s, it's fine.'

The Gap Between Women's Expectations and Reality

Many women on dating apps and at parties have clear criteria. Examples I actually heard:

- Annual income over 6 million yen (preferably 8 million)
- Height over 170cm
- Second or third son (eldest sons have parental care responsibilities)
- No job transfers
- Cooperative with housework and childcare
- Kind and takes the lead

How many men in their 30s meet all these criteria? While I cleared the income requirement, I'm 168cm tall and the eldest son. It was an uphill battle from the start.

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Changes in Market Value with Age

In my 20s, I thought 'older men are popular,' but it's different in your 30s. I particularly felt **market value drops sharply after 35**.

When I was 34, I received 'likes' from women aged 28-32. But at 36, the age range of matching women clearly went up, with almost zero response from women in their 20s. This change was quite shocking.

My Dating Failures

Failure 1: Pride Got in the Way Early On

For the first six months, I took completely wrong approaches:

- Didn't send 'likes' first (thought they'd come to me)
- Profile photo was my best shot from 5 years ago
- Inflated my income (listed 1 million yen more)
- Showed off with expensive restaurant dates

The results were terrible. Match rate below 5%, no second dates even when we met. **Good encounters don't come to men who can't let go of their pride**.

Failure 2: The Pitfall of the Numbers Game

After dropping my pride, I went to the opposite extreme with a 'numbers game' strategy:

- Sent 'likes' to 50 people daily
- Copy-pasted template messages
- 3-4 dates per week
- Juggling 5-6 people simultaneously

This was also a huge failure. I mixed up names, forgot previous conversations. Most importantly, I realized **I wasn't seriously engaging with anyone**. Naturally, this came across to them too.

Failure 3: Period of Pursuing Unrealistic Ideals

At one point, I pursued ideals too much:

- Only targeted beautiful women in their late 20s
- Required 100% hobby compatibility
- No compromise unless values completely aligned

During this period, I had almost no encounters. Even when occasionally matching, I'd dismiss them over minor differences thinking 'not this person.' It took a year to realize the obvious: **nobody's perfect**.

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The Turning Point: Mindset Reform and Strategy Change

Objectively Assessing My Market Value

After repeated failures, I first calmly analyzed my market value.

**My Strengths:**
- Annual income 6.5 million yen (above average)
- Stable full-time employment
- Good at cooking
- Good listener

**My Weaknesses:**
- Height 168cm (below average)
- Eldest son (potential parental care)
- Progressing hair loss
- Few hobbies

Accepting this reality, I developed a strategy to **leverage strengths and cover weaknesses**.

Revising Target Demographics

I had been targeting only late 20s, but realistically revised my targets:

- Main target: 30-35 years old
- Sub-target: 28-29, 36-38 years old
- Include divorced individuals
- OK with single parents depending on circumstances

This change **increased my match rate from 5% to 20%**.

Complete Profile Strategy Overhaul

The most effective change was completely revising my profile.

**Before:**
- Trying-to-be-cool self-introduction
- Hobbies: watching movies, reading (generic)
- Long description of ideal woman

**After:**
- Honest and approachable self-introduction
- Specific hobbies: weekend cooking (with photos of dishes)
- Simply wanting to build an enjoyable relationship
- Natural smiling photos by professional photographer

This change **tripled the 'likes' from women**.

Effective Dating Techniques I Practiced

Using Multiple Dating Apps Strategically

I ultimately used three apps strategically:

1. **Main app**: Paid app with serious users
2. **Sub app**: Major app with large membership
3. **Trial app**: Exploring possibilities with new apps

I slightly varied profiles on each to test **which approaches were most effective**.

Improving First Date Success Rate

Key points for first dates:

- Keep it under 2 hours (lunch or coffee)
- Meet near her station
- Prepare 3 conversation topics
- Focus on listening (70:30 ratio)
- Always send thank-you message same day

Practicing these raised **second date rate above 60%**.

Appropriate Management of Multiple Connections

I settled on a rule of **maximum 3 simultaneous connections**:

- Can properly engage with each
- No confusion
- Mentally and financially manageable

This number was my best balance.

Why I Finally Succeeded and What I Learned

'Honesty' Was the Key to Success

After 3 years of dating, the key to meeting my current partner was **'honesty'**:

- Answer honestly when asked about height
- Don't hide hair loss concerns
- Not embarrassed about cooking skills
- Sincerely express serious intentions for marriage

By showing my true self without pretense, I learned you can **meet someone truly compatible**.

Data on Success Rates for Men in Their 30s

Compiling data from dating friends around me:

- Married within 1 year: about 15%
- Married within 2 years: about 40%
- Married within 3 years: about 65%
- Over 3 years: about 35% (continuing or gave up)

**If you persist for 2-3 years, more than half succeed** - that's the reality.

Different Strategies by Age

Early and late 30s require different strategies.

**Early 30s (30-34):**
- 20s still within reach
- Can take time choosing
- OK to set slightly higher ideals

**Late 30s (35-39):**
- Speed is priority
- Realistic criteria setting
- Actively consider divorced/single parents

Switching strategies at 36 was my turning point to success.

Conclusion: Strategy is Everything for Men Dating in Their 30s

Dating for men in their 30s certainly has harsh realities. However, with **appropriate strategy and continuous effort**, good encounters will definitely come.

The most important things I learned in 3 years of dating:

1. **Objectively assess your market value**
2. **Drop pride and be honest**
3. **Set realistic targets**
4. **Don't give up, persist**

Practice these, and you'll definitely meet a wonderful partner.

Finally, to all men in their 30s struggling with dating: I also failed countless times over 3 years. But because I didn't give up, I have today's happiness. **Your efforts will definitely be rewarded**. I'm rooting for you!

Kentaro Sato

Kentaro Sato

Communication specialist applying business dialogue skills to relationships. Provides practical strategies with checklists and step-by-step guides.