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?




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