Chronically Single? 4 Reasons You Haven't Found Lasting Love (Yet)

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Author’s Note: The client described here is a fictional composite of actual clients.  Biographical information has been altered to protect the confidentiality of said clients.

Ellie arrives in my office for her first session.  She‘s visibly nervous.  As we sit and talk, she places her eyes intently on her feet, breaking away periodically to catch my gaze and smile shyly.

“What prompted you to come in for dating help, Ellie?”  

“Well, I guess I started thinking about it on my 35th birthday.”  Ellie explains that seeing forty looming in the not-too-distant future terrified her.  She worried that her long-standing singleness might be terminal.

“I haven’t had many relationships.  I’m not really sure why.  I’m pretty shy, but I would have thought I’d have more experience by now.”

As a therapist and coach who specializes in dating, I’ve heard Ellie’s story countless times:

  • Little to no dating in middle and high school
  • Low confidence
  • Few if any long-term relationships
  • First dates that never turn into second dates
  • Resentment, confusion, and hopelessness
  • A deep longing for love and no clue about how to find it

I assure Ellie that I have some ideas.  I’ve seen clients go from zero relationship experience to happy, long term relationships, including lost virginities and found marital bliss.

Now for the big question: “If you had to guess, Ellie, what stops you from finding love?”

Ellie squirms in her seat.  “Umm…I’m not sure, really. I mean, I don’t really meet a lot of people, at least not the kind I want to date.  I mostly do online dating, but that’s like a part-time job and doesn’t seem to go anywhere.”

Another common tale.  I tell Ellie that it sounds like she needs to work on the first of the Four Keys to Dating Success: her Dating Strategy.

1.   You Need a New Dating Strategy

You’ve heard it before -- dating is a numbers game.  You’ve gotta kiss a lot of frogs to find your prince/ss.

If you’re like Ellie and most “forever alone” singles, you may hyperfocus on one mate-finding venue, typically online dating.  You spend hours creating and looking at profiles, sending messages, and riding the Will-They-Message-Me-Back Rollercoaster.  

By the time you go on an actual date, you’ve thoroughly worn yourself out.  Add some dating anxiety (see #3 below) and suddenly every date is high stakes.

“This could be the one…oh, God, I hope so -- I’m so tired of online dating and I HATE how uncomfortable I feel on first dates.” An awkward coffee date later and no second date on the horizon, you may conclude that finding love’s impossible.

In the face of loneliness and dating fatigue, it’s easy to decide that “all the good ones are taken.”

Or “I’m just not attractive/confident/interesting enough.”

Or “online dating doesn’t work, especially for me.”

Maybe.  Or maybe you need a new dating strategy, one that optimizes your online dating efforts and widens your dating pool.

I walk Ellie through some basic online dating hacks to help her reduce the amount of time spent online and increase face-to-face dates. I also encourage her to spend more time meeting people offline.  We create a list of singles-saturated events and venues that she’s open to trying, including Meetup.com gatherings, social dances, and special interest workshops.

Ellie starts to look increasingly uncomfortable as we discuss increasing the number of dates she’s going on and meeting people offline.  When I gently point this out, she blurts out, “I don’t know if I can do all that! I mean, I totally draw a blank when I’m talking to someone attractive.  I hate small talk, so dates are really hard for me.”

I smile and reassure Ellie that there’s a solution for that, which is to develop the second of the Four Keys to Dating Success: Dating Skills.

2. You Need to Develop Dating Skills

I reassure Ellie that contrary to popular opinion, dating is a skill that can be learned.  

Many of us reach adulthood without having developed dating skills because we were simply never taught.  Your parents may have lacked social skills themselves, were too preoccupied to provide romantic mentorship, or actively discouraged you from dating entirely for cultural reasons.  

Ellie and I begin to review basic dating skills.  We role-play an approach and a first date.  I offer feedback to Ellie on body language, flirtation, and conversation skills.  I coach her on how to move from small talk to intimate conversation and incorporate attraction-building touch.

“This is good,” says Ellie, a bit more energized now, “but it’s much easier to talk with you here than it is to talk to an attractive person in real life.  I totally freeze up and my mind goes blank.  I’ll probably forget everything you’re telling me.”

Ah, well that’s another issue entirely.  And a very common one.

3.  You Have Dating Anxiety

I talk to Ellie about Social Anxiety Disorder (SAD), which is the crippling fear of being humiliated, embarrassed, or rejected.  According to the Anxiety and Depression Association of America, SAD affects 15 million Americans or 6.8% of the population.

You don’t have to be diagnosed with SAD to experience social anxiety – it’s a common human experience.  We’re not only wired to seek relationships, we’re also sensitive to being cast out of the pack.

Dating anxiety is a subset of social anxiety.  In dating related situations, it can cause you to:

  • Draw a blank and get unusually quiet
  • Become overly talkative and have racing thoughts
  • Avoid dating or approaching love interests entirely
  • Tremble, sweat, or blush
  • Feel overwhelmed with fear prior to dates
  • Ruminate and obsess after dates
  • Stop yourself from making a move for fear of offending or being rejected

I explain to Ellie that past experiences can prompt our brain to categorize dating as a life-or-death matter.  This isn’t conscious, of course.  But it sure is effective.

With dating anxiety, an attractive person walks in the room and our animal brain reacts as if a tiger’s barreling towards us, claws drawn.

We freeze.  We flee.  We even fight (often in the form of self-criticism).

Ellie and I discuss treatments for social anxiety: mindfulness, cognitive-behavioral therapy, exposure therapy and – a combination of all the above – drama therapy.

I emphasize that one of the best ways to overcome dating anxiety is to do the very things that scare you, gradually, intentionally, and with support.  Understandably, I see Ellie’s anxiety start to rise again.  I feel a  “yeah, but…” coming.

“Okay, so I can meet more people, improve my skills, and lower my anxiety.  But I don’t know if I trust myself OR the people I’m attracted to.  The few people I’ve dated have ended up to be jerks who disappear before we can get to any level of commitment.”

“That must be painful,” I respond.  And it’s another familiar tale, I tell her.  She’s talking about the last of the Four Keys to Dating Success.

4.   You Need to Develop Dating Wisdom

Ellie describes a typical and painful dating pattern: the Anxious-Avoidant Dance.

It goes something like this: you’re magnetized to someone and fall head over heels.  Things seem to go really well for the first date, week, month or even year.  And then disaster strikes.

Ellie’s most recent round of this dance was with Sal, a beautiful and outspoken co-worker.  Upon meeting, Ellie instantly felt that Sal was “the One.”

Ellie was on cloud nine when Sal asked her out.  But after a few hot and deep evenings, Sal turned cold, stopped returning Ellie’s texts and calls, and avoided her at work.

Ellie panicked.

She left text, voice, and Facebook messages.  She spent hours obsessing about what she did wrong.  

When Sal ignored all of Ellie’s attempts to connect and eventually began dating a different coworker, Ellie went into hyper-self-castigation mode -- “I shouldn’t have been so needy.  I should have just backed off.”

The Anxious-Avoidant Dance is set to the music of insecure attachment, a maladaptive way of relating in intimate relationships.  There are two common expressions of insecure attachment – anxious attachment and avoidant attachment.

Anxiously-attached people like Ellie fear abandonment, while avoidantly attached (a.k.a. “commitment phobic” or “emotionally unavailable”) people like Sal fear being consumed by a relationship.

Avoidantly- and anxiously-attached people tend to attract one another.  Perhaps because they feel familiar to one another.  They confuse fear for love and immediate infatuation for long-term compatibility.

Heller and Levine talk about this Anxious-Avoidant Trap in their book Attached: The New Science of Adult Attachment and How It Can Help You Find—And Keep—Love, which I heartily recommend to Ellie.

As we continue to discuss attachment, Ellie’s eyes sparkle and her gaze steadies.  “I can’t believe there’s something that explains what I’ve been going through!”

The Anxious-Avoidant Dance can be stopped with some education, self-understanding, and new behaviors.  I explain to Ellie that through our work, she can:

  • Explore and begin to heal the roots of her insecure attachment by looking more closely at her formative relationships from childhood.
  • Develop a secure attachment relationship with me, giving her first-hand experience of healthy relating.
  • Learn how to detect a love interest’s attachment style.
  • Identify anxious attachment behaviors and begin developing secure behaviors, e.g. effective communication and self-soothing.
  • Make conscious her own hidden relationship ambivalence, which prompts her to unconsciously choose partners who won’t stick around.

At the end of the session, Ellie and I review what we’ve discussed.  I assure her that it’s possible for her to break her pattern of chronic singleness by gradually improving her dating strategy, skills, confidence, and wisdom.

Ellie’s body relaxes.  She smiles, still shyly, but with a new softness in her eyes.  “Thank you.  I’m so happy there’s something I can do to change this.  I don’t want to be alone.”

I smile and reassure her, “You’re not anymore.”