How to Talk to a Midlife Solo.  By Dish Stanley

How to Talk to a Midlife Solo. By Dish Stanley

. 4 min read

Want to be more sensitive and compassionate? (Of course, you do!) Here are some easy tips to try.

Don’t Say:

“Why are YOU still single?” or “Have you met anybody special (yet)?” or “How is your dating going?” unless you’ve already had a conversation with them in which they made it clear both that they are dating and that they are comfortable discussing the status of their intimate life with you. There are so many ways that these questions can be hurtful. Here’s just a few:

Even in the best case, where your intentions are altruistic and your goal is to show you care about your friend’s happiness and well-being, unless they have invited you into a dialogue about this aspect of their private life it can feel intrusive. As my friend Paul said to me recently, “It is really a mash-up between ‘what’s wrong with you?’ And nagging.”  And even if you don’t intend it this way, my friend Sally says it can feel like somebody is asking about her sex life, when (of course) she’d never ask about the sex life of her married or partnered friends casually, out of the blue.

They may be happily solo and not interested in dating! In a worse-case scenario, you may be making an assumption about their life that conveys more about your own preferences, prejudices, fears or curiosity than about your interest in them. You may inadvertently be conveying that you don’t think their single life (or any single life) is as [fill in the blank — worthwhile, full, fun] as coupled-up life, which can be hurtful or insulting.

If they have been actively dating for a long time, it could be a downer for you to remind them of how hard it is to find someone. Think through how people in these circumstances answer this question. Usually deflated.

Finally, these pointed questions are so predictable they can just get boring. (‘OMFG. Not another dead-end ‘but you’re such a catch!’ Conversation.)

What I prefer is an open-ended question about what I’ve been up to or how my [summer/winter] is going that lets me take the lead on sharing what’s most important to me, what I’m excited about, etc. If I want to go into the status of my latest “situation” I will.

How to Ask If They Are Looking?

My favorite — and when I say favorite, I really mean the only acceptable way to ask somebody if they are looking for somebody — is the opposite of an open-ended question. I’ve come to the view (after an adventurous decade as a solo) that if a single friend has not initiated a conversation on their dating life with you, or affirmatively asked you to be on the lookout for them, the only circumstance and way YOU can raise this with them first is by mentioning a specific person you know who is looking. As the recipient of a thoughtfully constructed offer of introduction, it feels like I’m getting something that could potentially be useful from somebody who cares about how it lands with me.

It’s best to frame it in as narrowly drawn a statement as possible, so if they’re not interested everybody can quickly move on.

Here’s the formulation I recommend:

“A close friend in my department, David, is looking to date and he’s a [name something about David that may resonate with your friend] (for me it would be “and he’s a great golfer!). I told him I’d ask around, in case you know of anyone.”

The graciousness of this approach is that it allows the recipient to move in any direction they want, without feeling pressured or questioned or judged or having to worry about offending you by not wanting to meet your friend. They can say any of the: “I’ll think about whether I know anyone” to “Do you know whether he is ultimately looking for a serious relationship or just up for going out?” to “I’d love to check out his golf swing (LOL),” etc., etc. and etc.

Most importantly, you want to avoid unintentionally putting the single person in a position where they might have to defend why, even though they are single and dating, they are not looking to be fixed up with your friend.

What I (As a Midlife Solo) Wish My Partnered Friends Knew About Social Invitations:

I wish I had more coupled-up friends like my friends Nina, Steve, and Lisel, who issue plentiful invitations where neither your relationship status nor your gender is the threshold issue as to whether you get included. They have a wide circle of friends of both genders and varying relationship statuses. I think they just want everyone to have a wonderful time, so they ask anyone who might contribute to, and enjoy that particular gathering. Because their goal is a good gathering, and they make invitations with that as top of mind, their things are the funnest to be at for everyone.

I mean sure they do some (or a lot of) couples socializing, but that’s not the point. Nobody expects to be included in everything. Everybody does appreciate being included, feeling like their friends think they’ll be an addition to a social event, regardless of their relationship status.

If you love me as much as I love you (and I really do love you!), then please help me grow by forwarding this {love} Letter to a friend!  And I'd love to have you join us on instagram, facebook & twitter.

The Crush Letter
The Crush Letter is a weekly newsletter curated by Dish Stanley on everything love & connection - friendship, romance, self-love, sex. If you’d like to take a look at some of our best stories go to Read Us. Want the Dish?


'Merci'! to Emily in Paris for one of the most riverting women in pop culture "Divorce, Baby, Divorce" by Liza Lentini "Don't Touch My Hat.*" Midlife Men & Loneliness "This is a Tale of Modern Love ..." 2022 2024 Hit List 3 things I'm crushing on 5 Books to Help You Chill TF Out 5 Great Boutique Hotels Around NYC. By Jeanne Bosse 5 things that turn our crush readers on A Book That Could Unf*ck Your Relationship: I Want This To Work By Elizabeth Earnshaw. Reviewed By Angela Kempf. A Circle of Crones. By Elayne Clift A Roman Love Affair. By Lady Verity A Turntable and a Candle: F-ing Classics About Face: Skincare Essentials for Men An Upbeat Playlist for the Divorce-curious And I Wondered ... Do We Really Need A SATC Reboot? And Just Like That... Who Are These People?? By Jeanne Bosse And so this is Another brother gained and lost. By Jeanne Bosse Ask Dish Bedtime Rituals for Couples. By Lauren D. Weinstein Bisexually Anxious Among the Noodges. Review: shiva Baby Bloody Good Sex Book review Book Review: A Certain Hunger by Chelsea G. Summers Book Review: I'm With The Band by Pamela Des Barres. Reviewed by Evie Arnaude Book Review: Maurice Book Review: Norma Kamali: I Am Invincible Book Review: Swan Dive: The Making of a Rogue Ballerina by Georgina Pazcoguins. Reviewed By Lady Varity Book Review: The Confidence Game: Why We Fall For It Every Time By Maria Konnikova' Book Review: The Lover. By Marguerite Duras. Book Review: The Story of O Book Review: VOX by Nicholson Baker. Reviewed by Christian Pan Building The Perfect Music Collection Calm App Review: “If I Traveled Or Worked In An Office, I Would Rely On This App Heavily”. By Evie Arnaude Christian Pan CRUSH Summer Reading List! From CRUSH Reader Sharon Weinberg, Owner of The Chatham Bookstore Culture/Comments Dear Dish devour DEVOUR {things to do, have & know about} Devour: Reads we think you should devour Dish Gets A Kink Assessment. Dish Stanley Dish Stanley's Rules for Polite Society Doing Nothing With Friends Effortless, Natural Holiday Makeup. By Lauren D. Weinstein Emily In Paris Extended Encounters. By Lisa Ellex F*ck Songs. Three Best Jazz Albums for a Sexy Night In. By Lisa Ellex Facelifts: The Secret of Aging with Style and Attitude: Mireille Guiliano. Reviewed by Evie Arnaude Five Best Jazz Clubs Around The Country. By Lisa Ellex Foria's Totally Useful Guide to Sexting Four Indie Bookstore That Stayed In My Life Long After I Left Town. By Dish Stanley French Kiss: French Girls Do It Better, Right? friendship Fun in the sun skincare tips get your spy thrill on Girl Crush. By Lady Verity Grief. By Lauren D. Weinstein Healing Through Change. By Lauren D Weinstein Heard It at The Grammys: Dishs Crush on Silk Sonic Hefner. By Bob Guccione, Jr Hide A Love Note In Their Pocket. Hit List Holiday Invites Holiday Perspectives. By Dean Christopher Hook Ups Hot Thots How to Be the Most Charming Person at a Holiday Party. By Evie Arnaude How to find porn thats actually good I am my own family I just turned 60 but I feel 22 I redesigned my closet. I'm Dish, the Master of Ceremonies Im glad my mom died In Good Hands. Kathy: This Is A Love Story About Three Friends La Mia Famiglia by Lisa Ellex Lamentations on the Lost Art of Kissing. By Elisabeth C. Lamotte Leave the husband, bring the cannoli. By A.K.A. Darla Let's Reconsider, with Adam Grant Love & Mike's "Bad Girl Pasta" Love/Sex/Moon Magick By Lynn Eaton LXIX. By A.K.A. Darla Meeting Across the River Melissa Biggs Bradley's New Book Safari Style Makes Me Want To Go On A Safari midlife MIDLIFE CRISIS: When Reality Strikes, By Dean Christopher Movie Magic. By Amy Ferris My First Solo Trip: Mexico, Part I. By Dawn Larsen My Prostate Journey: A Personal Story My Tits Contain MulTITudes Naked & Not afraid by KC Roth Oasis in the Desert. One woman's honest journey through vaginal rejuvenation. OMG Yes. Pamela Anderson: What Her Story Says About Us paris Pillow Tawk (or NOT)? Play well with others. By Dish Stanley Playing Games: A Review of Esther Perel's New Sold Out Card Game. Podcast Review: Dying for Sex. Why You Need to Listen to Molly's Journey. political thrillers PrimeCrush & Chill: Movies Worth a Re-Watch PrimeCrush Bookshop PrimeCrush Cocktail Coaster Giveaway! QUIVER. Sexual Debut Stories. recommedations Red Flags Reports from the edge. By Jane Boon separate bedrooms Sexual Frustrations. By Elisabeth C Lamotte Shameless Quick & Easy Mac & Cheese. By Evie Arnaude Sighs & Moans. By Ralph Greco SIP. Best Lines from the Double Dates Podcast Hosted by Marlo Thomas & Phil Donahue Six Ways to Get the Friends Who Count Snapshot Rec: Get Yourself Sexify-ed on Netflix. Snapshot Rec: Read Liza Lentini on the Indigo Girls in SPIN Solo in my Sixties. By Jeanne Bosse Songs That Make You Wanna F*ck. Stanley Tucci Is Paradise Stories to Read Aloud to a Lover. By A.K.A. Darla Tell Me More. By Dish Stanley The 3 Things You're Really Fighting About The 4 Most Common Skincare Issues for Men (But Were Afraid to Ask). By Lauren D. Weinstein The Crush Letter 44 The Crush Letter 51: DEVOUR The Crush Letter 58 the crush letter 72 the crush letter 73 The Crush Letter 75 the crush letter 77 The Crush Letter Its a tune The Crush Letter No 33 The Crush letter No 36 The Crush Letter No 39 The Crush Letter No 40 The Crush Letter No 41: DEVOUR The Crush Letter No 42 The Crush Letter No 43 The Crush Letter No 45 The Crush Letter No 46: DEVOUR The Crush Letter No 50 The Crush Letter No 53 The Crush Letter No 54 The Crush Letter No 55 The Crush Letter No 56 DEVOUR The Crush Letter No 57 The Crush Letter No 59 The Crush Letter No 60: DEVOUR The Crush Letter No 61 The Crush Letter No 62 the crush letter no 63 The Crush Letter No 64 The Crush Letter No 65: DEVOUR The Crush Letter No 66 The Crush Letter No 67 The Crush Letter No 68 The Crush Letter No 69 The Crush letter No 70 The Crush Letter No 74: DEVOUR The Crush Letter No 78 The Crush Letter No 80 The Crush Letter No 81 The Crush Letter No 82 The Crush Letter No 83: DEVOUR The Crush Letter No 84 The Crush letter No 85 The Crush Letter No 86: The Toy Tester Report The Crush letter No:71 DEVOUR The Crush Letter No. 79 The Crush Letter No. 94 The Crush Letter: Culture / Comment The Dynamics of Friendhip By Lauren D. Weinstein The Friendship Files By AKA Darla The Golden Bachelor The Hole. By Kiva Schuler The Holiday Anti-Checklist By Liza Lentini The New Menopause By Dr. Mary Claire Haver The Perfect Snowy Saturday. By Jeanne Bosse The Ritual of Comforts. By Lady Verity The Sex Position Report. By Dish Stanley The Solo Series Thee Timeless Travel Books. By Bob Guccione Jr. Things To Let Go Of. By Dish Stanley This must be the place To get all of us, subscribe. Top Ten Jazz Albums To Soothe Your Soul. By Lisa Ellex TOPIX Transitions Travel tips Treats: A Sex Toy Tester Update Under The Radar Series. By Dish Stanley Valentines day what dead to me taught me about family. Who Are CRUSH Readers Grateful For? Women of a Certain Age Whose Style I Admire You're My Medicine Your Big Green Heart. By Liza Lentini Your Love Is King & Queen, GQ Zits a poppin Zoning Out in Comfort. By Dean Christopher