Ask A Shrink: Better Off Alone?

Accidentally found yourself in bed with your best friend's wife? Thinking about leaving your high-paying gig to pursue your passion? Inexplicably dumped — AGAIN? From navigating your neighbor-crush to overcoming your crippling fear of toaster pastries, it's all fair game when it comes to your psychic life. Each week our resident shrink will take up your questions about loving, living, and working in the Bay Area and beyond.

I'm a late 30s female living in the Bay for a couple of years. I was working for a startup that ran out of cash, so I've been trying to network and get a new job for a few months now. I've been single for about 10 years — longest relationship in that time was a few months or so.

Is it worth continuing to try dating when I've had so little success finding someone that's both a decent human being and interested in dating me? I feel like it's pointless — no matter how many different people I try dating, or meeting in different ways, it just ends up either disappointing or worse, damaging to my self-esteem.

Dear Better Off Alone,

Wowee! So early on in Ask a Shrink's career, you have forced me to whip out my psychoanalytic hat and address — you guessed it — the transference!

Here's what I mean by that, BOA. You've stated that you've been flying solo for 10 years. You've yet to find someone who is both a tolerable person and interested in you. The disappointment is pointless and causes further damage to your already-pummeled self-esteem.

And yet here you are writing in for advice about whether or not to continue looking for love, when all signs point to: NO! Give up! Get out! Flee! Before it's too late, before the last shards of your dessicated heart are caught up in the wind and dispersed among craft cocktails and flaked on artisanal toast. (“I call this drink the “Crushed Soul.”)

And yet…

I suspect you are looking for my permission to maintain hope. Despite the suffering, despite the hardship, despite the long and painful nights binge eating Kettle Chips and streaming GoT (oh wait, what?*), a part of you desperately wants to believe that a warm, loving, mutual, connected relationship is possible — even for you.

Hence the transference: You're looking to me to be the person who buttresses that hopeful part of you. I'm more than happy to oblige.

Of course, shrinks aren't fortune tellers (or are we…), so I cannot say if it's going to work out for you, but I would encourage you to notice and nurture that little part of you that still aches for intimacy. Don't let it die! Feed her, whisper kind things to her, fluff out her adorable cotton ball curls. Attend closely to the part of you that desires love.

That being said — perhaps step back from the dating scene for a few weeks, yeah? With the job loss and then the job hunt — you've got a lot of stressful shit going on and all of this certainly takes an emotional, psychic and physical toll.

If your heart's taken a beating, then dating can be a huge stressor. Taking the risk to be vulnerable in one area of your life requires that you have a stable foundation in other areas of your life. When that fabulous OkCupid date suddenly excuses herself for a call and never returns, it is vital that you have a solid cushion of support — friends, family and financial stability — that can serve as a respite in the Tornado of Bullshit that is dating.

Set aside a tolerable amount of time to abstain from the dating scene and, instead, make a concerted effort to focus on investing in your friendships, your professional life and your emotional wellbeing. Take up activities like writing in your journal, exploring Golden Gate park, participating in Sidewalk Talk (, knitting sweaters out of cat hair and, of course, finding your very own psychotherapist.

*Countertransference (

Tiffany McLain has a psychotherapy practice in San Francisco where she specializes in working with young professionals who straddle multiple identities — be this professionally, ethnically, or economically. She has been featured in Huffington Post, Psychology Today, and Psyched in San Francisco Magazine. Find out more:

Disclaimer: Though Tiffany is a licensed professional, this advice column is not therapy. It is for education and entertainment. Use at your own risk.

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