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<Struggling to Connect: Why Am I Still Single Despite My Efforts?>

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By Harris O’Malley

Dear Dr. NerdLove,

I hope you're doing well. I've been following your column for some time and feel you could help with my situation. I'm a 25-year-old guy who is still single and tired of being a virgin who hasn't even held hands with someone. I've been actively trying to make myself more appealing to women, but despite my improvements, I can't seem to form any genuine connections. It's leaving me confused and frustrated.

After being dateless for so long, I decided to invest my time in becoming the ideal man that women often describe. I've consumed countless articles and videos on how to be the type of guy that women find attractive, and I've put these insights into practice.

Over the last few years, I've focused on various areas of my life to become a better version of myself. I've been working out, eating healthily, making new friends, and exploring interesting hobbies.

People frequently mention that women are drawn to confident men with a good sense of humor, so I've been making an effort in that area as well. I'm trying to be self-assured without being arrogant, and I'm not hesitant to share jokes and enjoy myself.

One significant area I've been developing is my emotional intelligence. I've taken to heart your insights about women's expectations and have been working on being more empathetic, understanding, and supportive. Additionally, I've been honing my communication skills to connect with others on a deeper level.

However, despite all this effort, I still face rejection or worse. Women claim to want men who are open about their feelings and can be vulnerable, yet whenever I try to be sincere, they react as if I'm being strange. I'm not talking about breaking down over a past pet’s death, but simply showing a bit of vulnerability or active listening leads to them calling me weird.

What perplexes me the most is that they seem to prefer guys who don't exert even half the effort that I do.

This situation is quite disheartening. I can't help but question whether there's something wrong with me or if I'm simply not doing enough. It feels like an uphill battle, and I'm at a loss for what to do next.

Doc, I could really use your advice. I'm exhausted from feeling inadequate, and when I attempt to be what women claim they want, I get shot down. Am I overlooking something or making a mistake? How can I forge real connections with women?

Doing The Work

Since you’ve been reading my column for a while, DTW, you might recall my advice that self-improvement should be for your own benefit, rather than solely to attract women.

This is the crux of the issue. You might find yourself feeling frustrated after putting in so much effort—effort you should be proud of—only to see it not yield the expected results.

There are two significant disconnects that likely contribute to your struggles.

The first is your reliance on “what women say they want” as a definitive guide. While some aspects ring true—like the desire for better communication and emotional availability—preferences vary widely from woman to woman. Popular posts on platforms like Reddit or TikTok may garner attention, but that doesn’t translate to a universal checklist for what all women want.

A common mistake is attempting to shape oneself into what one believes women desire, often resulting in losing one’s authentic self. This effort can feel like trying to fit into someone else's mold, leading to discomfort and an inauthentic persona that others can sense, which can be off-putting.

Self-improvement isn’t about becoming someone else; it’s about becoming the best version of yourself. It’s essential to embrace your unique qualities rather than trying to conform to an external ideal.

It's also worth noting that our understanding of ourselves is fluid. What we consider as our “identity” is often shaped by limitations we’ve placed on ourselves. Trying new things or adopting new styles can reveal facets of ourselves we didn’t know existed.

That said, it's crucial to engage in activities that genuinely resonate with you instead of merely pursuing what others deem attractive. Enjoying fitness or new hobbies is wonderful, but they should stem from your interests rather than external expectations.

The second disconnect lies in the belief that making changes will instantly lead to rewards. Let’s take emotional intelligence as an example. While you’ve worked on being more open and empathetic, simply expressing your emotions isn’t enough. Emotional intelligence encompasses knowing when and how to share those feelings.

Men often encounter difficulties in developing emotional intelligence because it can be unfamiliar territory for many. A man who can express vulnerability and understand others’ emotions might be seen as unusual, especially if they are more accustomed to emotionally closed-off men.

Part of cultivating emotional intelligence involves recognizing this dynamic.

Moreover, some women may approach emotionally expressive men with caution due to past experiences with individuals who misrepresented themselves as sensitive but were actually predatory.

Displaying your emotional growth shouldn’t be a means to gain approval; it should enhance your life and improve relationships. The goal is to become a better partner, not to guarantee a partner.

I recommend taking some time for self-reflection. Examine how much of your current self is genuinely you versus who you feel you should be. If you're not in touch with your authentic self, how can others connect with you?

Some of your changes might need reevaluation. Returning to basics and approaching your life with authenticity rather than merely fulfilling a checklist could be beneficial. People will be drawn to the best version of you, not a façade of what you think women desire.

And remember, your efforts have not been wasted. You’ve made significant progress, and it’s okay to acknowledge that the journey of self-discovery can lead to missteps. Viewing this as a learning experience about your true self rather than a setback is essential.

Good luck.

Hi Doc,

I've recently started reading your column, and it's incredibly insightful. I’m reaching out for advice because I feel overwhelmed.

My girlfriend and I have been together for 5.5 years, and we’re very much in love. We’ve discussed our future together, but I have concerns about our sex life. My girlfriend has always presented herself as adventurous, yet there are times when intimacy is lacking. We’ve talked about our physical connection, but I feel it should be more frequent since we only see each other three days a week.

I struggle to contain my emotions, and when intimacy is denied, I tend to become distant. Despite my efforts to improve our sex life, I still feel that once a week is insufficient.

I feel guilty for my feelings, especially knowing how special she is, yet my frustration leads me to seek other outlets for relief.

Could you help me understand if I’m in the wrong or suggest ways to address this?

Frozen Out

To begin, I want to clarify that once a week isn't necessarily a bad frequency for a couple together for nearly six years, especially if you only see each other three times a week. However, I understand your desire for increased intimacy, which is entirely valid.

That said, I wonder if the frequency is the main issue or if other factors need to be considered. Sometimes focusing solely on how often sex occurs—presumably penetration—can obscure potential solutions or compromises.

I wish I had more information, FO, because I have many follow-up questions. First, what does "down for anything" mean? It’s a vague phrase that could imply she's open to trying new things or willing to engage in sex at any time. Misunderstandings about this could be at the root of your concerns.

I’d also like to know what you feel is lacking with only having sex once a week. Are you seeking more physical pleasure, or is sex integral to feeling connected and valued by your girlfriend?

Understanding the underlying issues is key to addressing your concerns. Sometimes, what you’re asking for isn’t aligned with what you truly desire.

However, the most pressing question is whether you've discussed your girlfriend’s feelings on the matter. How does she feel about your current sex life? Is she frustrated with the frequency, or does she have a lower libido? Are there external factors affecting her desire?

Your awareness of becoming distant when feeling “denied” is concerning. Framing your frustration as being “denied” can create tension. It implies entitlement to intimacy, which may not be the case. Even if unintended, this perspective can create emotional barriers.

Additionally, distancing yourself can feel like punishment for her not wanting sex, which could breed resentment. If she’s dealing with personal issues, your reaction may exacerbate her feelings of inadequacy.

This highlights the need for an open and honest conversation. While you’ve addressed your issues, have you truly been vulnerable about your feelings?

Schedule a time to talk when you both won’t be interrupted. Share your feelings and explain what you’re missing, but avoid simply saying “I want more sex.” Articulate your feelings, why they matter, and potential solutions.

After expressing your thoughts, invite her to share hers. Listen to her perspective without interruption, and ensure you understand her feelings by paraphrasing her points back to her.

Once you both grasp each other’s perspectives, seek compromise. If her desire is affected by various factors, consider how you can support her without pressuring her. Alternatively, you might redefine what “sex” means to both of you, exploring intimacy beyond penetration.

Massages or non-sexual intimacy can foster connection without the pressure of sexual expectation. Conversely, you may need to explore personal avenues for relief, like self-pleasure, during times of unmet intimacy.

Lastly, if you're aware of your distancing behavior and continue it, consider seeking counseling to address why this pattern persists. Recognizing harmful behaviors is the first step, but actively working to change them is crucial.

This might also be the key to preserving your relationship.

Good luck.

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