What do you do to get yourself back up after disappointment, anger, frustration ….? For me, it’s going for a jog — the slower and sweatier, the better! Get in in touch and tell me your tricks.

Kerry says this pic with her son is one of her favorite snaps.

Me, after a 4.7-mile jog. It was “only” 75 degrees when I started.
Transcript
LAURA STASSI
I love doing this show. But I confess, there are times when I get so immersed in other people’s dating and relationship stories that I neglect to reflect on my own journey and come up with a solid game plan for what to do next. So it really struck a chord when I received an email from this listener.
KERRY
So my name is Kerry. I’ve been working as a psychotherapist for about the last 25 years, and I love what I do. I’m passionate about what I do. I think it’s been like a real privilege for me because it’s given me such an opportunity, not only to do something meaningful with my life, but I’ve learned so much from this job.
LAURA STASSI
You wrote to me a while ago and the first line really got to me. You said you were bereft of hope. Let’s go back to the headspace that you were in when you wrote that.
KERRY
Well, first of all, I should preface this by saying I’ve been single — I’m using air court quotes because it in my mind that means not married in this context — for almost 23 years, and so I’ve had a tremendous amount of, let’s just say, experience dating. Now, I’ve had several long-term relationships in that time, but it’s been a real struggle for me finding a lifetime partner. And so on that day, I had been seeing someone, and there are these really interesting Facebook pages for women who are looking to gather information on who they’re going out with, to see if anybody else is dating them, and I had gone on that page and noticed that someone was asking about someone I’d gone out with, someone much younger, you know, kind of inappropriately younger.
LAURA STASSI
Oh boy.
KERRY
I had had a conversation with a client of mine earlier who sort of shared a similar experience, and you know, I think just maybe that in context with this long history, um yeah, I was feeling fairly down. And something happened after I hit the send button, Laura, which was I had to sit with this, right. I sent you this message and I had to sit with, I’m a big fan of radical accountability, right, and really sitting with –well, Kerry, you pick these people, honey, right, like you are making these choices, and you really need to look at that and think about the part you play in making choices that have not worked out well for you, which is hard sometimes. You know, to take responsibility for the relationships that have — you know, some of them, I don’t think it would be a stretch to say, wreaked havoc on my life.
LAURA STASSI
So you said that you have been dating somebody and you went on a page to find out if he was dating someone else, and you found out.
KERRY
Yeah.
LAURA STASSI
Was it the fact that he was dating somebody else, or that it was somebody else younger? I mean, did you think you were exclusive?
KERRY
Yeah, no, I didn’t think I was exclusive. I think it was just the fact that the person that was making that inquiry was young enough to be my daughter, right, and I and I was just like, well, kind of recoiled a little bit and so, but no, I was not under the impression at that point that we were exclusive.
LAURA STASSI
Okay.
KERRY
Together with the conversation that I’d had with that client of mine who sort of reported something very similar and just sort of you know like in addition to sort of this very long history of, let’s just say, a lack of success.
LAURA STASSI
On the one hand, you were feeling very emotional, it sounds like because you also said you — it sounds like what you’re looking for you’re not finding in men your own age or in men that want a woman your age.
KERRY
I’ve always wanted to date in the same age range and, yeah, I’ve been having a really tough time. Um, and maybe you know I’ve often wondered are my standards too high? But I don’t think that’s the case now, Laura. It was the case that I was walking by red flags the size of Texas, making excuses, right and just and I think, to some degree, because of the way I looked at being single and you know, looking at being single as a problem. You know, everybody’s coupled up and there’s really not a lot of conversation around or you know anything with regard to looking at being single as a positive, right?
LAURA STASSI
So I want to go back a minute to red flags the size of Texas. Can you give us an example?
KERRY
Oh gosh, I mean, this is quite a story and this is, I guess, ties into the you know, the sort of the shame of this. But there was a gentleman that I was in a relationship with who, oh wow, had a job in big pharma at one point and, you know, he and his fellow employees, and this particular company as well, were engaged in a practice that was illegal. And, you know, four months into our relationship, he had told me he had a business meeting down in Charleston. Oh, this is horrible — and is driving back from that meeting one Wednesday evening, and we’re having a conversation on the phone and I said so how was your meeting? And he said well, I have a confession to make. Are you sitting down?
And I said yes, and he said, I did not go down to Charleston for a business meeting. I went down for a sentencing hearing. And honestly, I mean, he was an adorable human and very smart and had a lot, and that’s, I guess, that’s the thing that’s always interesting about people too. You know, they’re neither. At least, I’ve never met anybody who’s either all good or all bad.
LAURA STASSI
Right.
KERRY
And we sometimes make decisions that are regrettable. And without going into too much detail, when he explained it to me, I could see how someone could kind of get pulled into you know, the whole organization is doing it and everybody’s doing it, and it’s just sort of common practice and we’re just doing it, right.
BREAK
LAURA STASSI
You’ve been single for over 20 years.
KERRI
Yes.
LAURA STASSI
And I’m wondering, when you first became single, if you prepared yourself to start dating again or, you know, through the years have you done anything different?
And the reason I ask this I remember talking to a woman when I first got divorced and I’d found out at the time that she had been dating. I think it was 13 years at that point and she had been on Match continuously. She kept just renewing her Match membership and she was getting a ton of dates on it, but after a couple months, you know, something would happen. And what she kept telling me is oh, this is all practice, this is all practice. And I remember I was totally confused and at one point I said okay, practice for what?
KERRY
Well, you know, life is a practice.
LAURA STASSI
Right. For what, though? But so, and that’s what I’m wondering, if and again, not to put you on the spot, not to judge, I’m just curious is to have you been doing the same thing that you’ve been doing since you became single?
KERRY
You know, I don’t think so, and maybe that’s just my ego wanting to say no, but I think what has happened is, you know, over the years, I mean, I do see life as sort of this practice. It’s a journey towards greater self-awareness, right, and as a woman in my mid-30s, did I really know myself back then? No, you know. And so part of this, and it’s really interesting how, in relationship to other people, you know, it can help us gain greater self-awareness, right, and so that has helped.
And there have been times that I’ve thought okay, Kerri, you need to think outside the box. You’ve been sort of looking for this one particular sort of type of person, and it’s funny because my first adventure outside of the box was the gentleman I just described to you, that had the red flag.
I think I think what I really needed to sit with was that I wasn’t really allowing myself the time to really wait for what it was I ultimately wanted. You know, after I sent you that message and I really sat and I thought about it and I sort of had this, you know, moment of personal confrontation. Like what are you doing? Why are you doing this? You know, why are you coming at it with this energy of, this is a problem to solve, when life has always been more peaceful on your own, you’ve created a wonderful life for yourself. Why are you also meeting people who aren’t really, ultimately, what you’d like to settle down with long-term, and why don’t you just stop doing that? (Laughter)
LAURA STASSI
Well, that takes a lot of emotional clarity to understand that, right?
KERRY
Yeah. Well, it’s been a long time, dear. It’s interesting because once I had this internal shift and this recognition of, okay, what are you doing and how are you coming at this and what is your energy behind this, that all of a sudden — and I don’t know what the magic of that has been or whether it’s just been I’ve been thinking a little bit more about it when I, when I look at the you know the people that I do come across on this one dating app that I’ve used, for whatever reason, there’s three people that I’m talking to now.
As much as I’d love to have a partner that I’m deeply connected to, there’s also a lot of really wonderful and beautiful things about being single that that I don’t think I was really embracing. And, look, you know, I don’t think it’s how people are really wired. I think we’re wired to be in connection and in relationship, but maybe there needs to be a shift. Certainly, there needed to be one for me to like, also, looking at you know, how rich my life was as a single person and really, like — I don’t know, sinking into the loveliness of that.
LAURA STASSI
Kerry says that initially, she was reluctant to share her story. She’s kind of embarrassed, given her profession. But she decided to talk because she wants anyone struggling to understand that they are not alone. And she hopes anyone looking for romantic companionship does not settle for less than they deserve, merely because they are uncomfortable with being alone.
Funny how life works. Since Kerry and I spoke, she’s now in a promising relationship with one of the men she met online. She says he’s patient and has a great capacity for understanding and communicating, and she’s grateful to have met him.
END CREDITS
Speed Dating While Gray audio production and mix is by Steve Lack: Audio. For more on the show, including how to get in touch with me, go to datingwhilegray.com. I’m Laura Stassi. Thanks for listening.
Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email laura@datingwhilegray.com.