On Being ‘The Grenade’

Dearest Rachel – I’ve spoken to certain people who find themselves amused at some of the stories I tell you about my life lived after you, particularly those having to do with finding a successor to you (if you’d want to call her that). It offers a measure of comfort to me that, if IContinue reading “On Being ‘The Grenade’”

There’s No Way to be Subtle

Dearest Rachel – I’ve spun more than a few tales about my misadventures – and misgivings – in attempting to find romance via online sites and apps. Given that I have no idea who I might or might not be dealing with out here in cyberspace, I’m moving at a snail’s pace, because I’ve comeContinue reading “There’s No Way to be Subtle”

Spaces In Our Togetherness

Dearest Rachel – These days, Ruby will occasionally ask me whether I’ve spoken to another woman, especially if I don’t contact – or respond to – her on Google Chat quickly enough. Maybe she’s worried that she’ll lose me to someone else too early in the game, in which case I suppose I should beContinue reading “Spaces In Our Togetherness”

Real Life Rickrolling

Dearest Rachel – I would like to think that I wouldn’t have to explain the concept of the rickroll to anyone on the internet. Anyone who’s been out here any length of time has probably been conned into clicking a link that took them to Mr. Astley’s music video, and those who haven’t, really justContinue reading “Real Life Rickrolling”

When Wheedling Won’t Work

Dearest Rachel – When I first joined this dating app, Jeff (who’d met his wife on one a year or two back) warned me that I should prepare myself to face a hundred rejections or so before finding anybody. Surprisingly, that hasn’t happened thus far. But what has happened has pushed me very nearly toContinue reading “When Wheedling Won’t Work”

Found

Dearest Rachel – You’ll recall me mentioning the other day when I was wandering around Basel how you’re never truly lost; that it’s just a matter of not being where you want to be. As a consequence, being ‘found’ isn’t the opposite of being lost; it’s just a matter of someone else realizing where youContinue reading “Found”

They Can’t All Be Gems

Dearest Rachel – I know I have permission to skip a day or two now and again, but that wasn’t how life was like when you were still here. There was rarely a day that went by that we didn’t talk to each other. I mean, there were occasions when you were out of town,Continue reading “They Can’t All Be Gems”

Spooky Stuff

Dearest Rachel – Yes, I know Halloween was over three weeks ago, but the days continue to get shorter, and the nights continue to get longer – and there are still spooky things that come out of the woodwork as time goes by. I woke up this morning with an idea in my head toContinue reading “Spooky Stuff”

Adhesiveness in Anytown

Dearest Rachel – Last night, after a few hours of gaming with Kevin, I found myself in conversation with another individual on the dating app. She’d sent me a smile, and while I generally tend to limit my connections to those residing here in Chicago and the surrounding suburbs, I couldn’t quite figure out whereContinue reading “Adhesiveness in Anytown”

The Shoe Finally Drops

Dearest Rachel – I teased about this the other day, because it was happening almost at the same time I was writing about dealing with another scammer on the dating app. But this one was longer in coming around. In fact, I was wondering if it would even actually happen. But I think I knewContinue reading “The Shoe Finally Drops”

The Power of the Ping Compels Me

Dearest Rachel – I promised myself that I wouldn’t be suckered by these ladies. But I have to confess, I’m almost incapable of leaving anybody on ‘read.’ I try not to start a conversation, but if someone addresses me, I almost always feel the need to respond, even if it’s only out of sheer courtesy.Continue reading “The Power of the Ping Compels Me”

Is It Really ‘Just A Number’?

Dearest Rachel – In my continued adventures in online dating, I’ve noticed that ones who have been responding to me have tended to be younger than myself. Coming from a cultural background where that’s more the rule than the exception (sure, there are plenty of couples where both are more or less the same age,Continue reading “Is It Really ‘Just A Number’?”

Curiouser and Curiouser

My! People come and go so quickly here! Dorothy (Judy Garland) observes Glinda’s departure in The Wizard of Oz (1938) Dearest Rachel – You’d probably take me to task a bit for conflating Dorothy Gale… …with Alice Lidell… …just for the sake of an interesting title and quote to lead this letter off with. YouContinue reading “Curiouser and Curiouser”

A Saturday Off

Dearest Rachel – There’s about two hundred guys up at camp this weekend. Neither Daniel nor I are among them. Needless to say, this Saturday seems… off. Normally, at this hour, I’d be returning from the Bible study, probably after running an errand or two in the process. I won’t say that I’ve been thereContinue reading “A Saturday Off”

If You Laugh at Different Comics…

…If you root for different teams,Waste no time, weep no more,Show him what the door is for.Rub him out of the roll callAnd drum him out of your dreams. Oscar Hammerstein II, “I’m Gonna Wash That Man Right Outa My Hair”, South Pacific (1949) Dearest Rachel – I mentioned before about the fact that thereContinue reading “If You Laugh at Different Comics…”

A New Theme Song

Dearest Rachel – I think I’ve mentioned the joke before in these letters, and when we were all watching certain meme channels, we were familiar with it, but it bears repeating: if you think of your life as a television series, your alarm clock is basically your theme music, since it’s what starts each episode.Continue reading “A New Theme Song”

The Games We Must Play

Dearest Rachel – For all that I said the other day about women who insist that they don’t want someone who ‘plays games’ – and yet they inevitably play games themselves – the fact of the matter is, there is really no getting away from playing games in this process of finding someone to fillContinue reading “The Games We Must Play”

Replacement

Dearest Rachel – Well, if it’s here at church, no one’s seen it. So tonight, I bought myself a replacement Grief Share workbook. The few bucks spent on it are of little concern, but I’m none too thrilled about losing four weeks of notes. Still, this ought to guarantee that the old one shows upContinue reading “Replacement”

The Point of Deception

Dearest Rachel – I had originally planned on writing you about how nice it was to have conversations first thing in the morning… but then, things took a bit of a turn. And I’m afraid this isn’t really a trip down memory lane. More often than not, while I would make a point of kissingContinue reading “The Point of Deception”

Only From A Distance

Dearest Rachel – I haven’t talked to you all that much recently about how things are going on the dating front. Not because I think you’d be jealous (while you never explicitly gave me the permission to find someone else after you were gone like I gave you, I’m pretty sure that your reaction whenContinue reading “Only From A Distance”

Giddyup, Four-One-Nine

Dearest Rachel – Among the many channels that we used to entertain ourselves with on YouTube, both before and during the lockdown (and you probably see where this is going, but the rest of the folks reading this might not), there was a fellow by the name of James Veitch who had a particular talentContinue reading “Giddyup, Four-One-Nine”

Do Nothing Slowly

Dearest Rachel – When my dad retired about ten years ago, he quoted the legendary pitcher Satchel Paige as to how he was going to spend his time: I’m going to do nothing, and do it slowly. That has summed up a number of my days since quitting my job, too – especially in thoseContinue reading “Do Nothing Slowly”

And So It Begins

Dearest Rachel – So here we are. I never thought I’d be doing this again; maybe that’s part of the point. Maybe this partly some form of karmic punishment for not having taking you on enough dates back when I had a chance. It’s true that when you’re married – especially for a lengthy periodContinue reading “And So It Begins”

Unsettled

Dearest Rachel – It’s a challenging thing to try to navigate the ocean that is the dating pool. I chatted with a woman who seemed frustrated that the men she was meeting didn’t seem to know what they wanted out of a woman. Since I didn’t see her as a potential match (and therefore wasContinue reading “Unsettled”

Not In Crazy

Dearest Rachel – I understand that there’s an old saying about relationships: “Don’t stick your [neck] into crazy.” I’m pretty sure I’m off by a couple of letters there, but I think you get the idea. I bring this up to update you on the story of the, ah… woman? bot? that I spoke ofContinue reading “Not In Crazy”

Sunday Rush

Dearest Rachel – After a couple of days of relative quiet upon enrolling on this dating app, starting this morning, things went somewhat crazy. I’m not complaining, exactly, but the ‘feast or famine’ situation – if this is what the typical experience is like – is a bit disorienting. As I mentioned previously, for theContinue reading “Sunday Rush”

A Touch of Nervous Energy

Dearest Rachel – What with having woken up before six o’clock on a Saturday to shower and tend to the dog (although in fairness, I actually managed to do the former without waking up the old guy! Huzzah!), making a point to attend this morning’s Bible study, followed by running about on errands until aboutContinue reading “A Touch of Nervous Energy”