Vol. 2, Post #63 For The Menfolk

Here's how to ask out a woman my age. My weekly sex tips for girls* (*girls who are holding on to mid-life by a thread). A dating odyssey for Young Olds, (people with readers).

I got a message last week that was kind of adorable but also made me think that sometimes we might take for granted the basics that go into healthy dating when we’re dealing with someone who is just now starting to explore after a long partnership/marriage has ended. And IN PARTICULAR, I’m going to gear this one towards the menfolk, so pull up a chair, Boys.

(My pals at Jenny Magazine recently did a poll - Lloyd Dobler or Jake Ryan? I mean, there’s no contest in my book, so here’s a low-hanging-fruit image for ya. If Lloyd was a single Young Old today, I imagine he’d maybe send a similar message to me, like the one I’m about to share, below. That Lloyd, he proudly has no game. Probably why he’s such a panty-soaker. Trivia: John Cusack put a scar on his right eyebrow for Lloyd's character. He says that the story behind that is that someone threw a rock at Lloyd when he was a kid.)

So, back to biz. A male reader sent me this after reading about how I’m a sex-starved crone (I kid. About the crone part). Here’s an excerpt:

You might think this sounds ridiculous, but I’ve not dated for a long time, and I don’t really know how to best pursue a woman, in terms of taking a conversation to the next step and going out. If I connect with a woman on an app, how fast should I ask her out if we start messaging back and forth? Some women seem to like to endlessly “chat” and others seem annoyed if I don’t make a move and for that matter, a lot of my female friends (most of whom are married, so not sure they are right about this) said I should suggest something fairly benign like a walk, but doesn’t that seem like a lot for a first meet up? The other question I have is this: I’m assuming I do the asking out, right? Even though I know most women value equality, I think they want me to make a plan, but again, I’m a little clueless. I seriously haven’t dated since my late 20s. Besides all of that, and I hope this doesn’t sound like a line, but I’m sure you get asked out all the time, and I think you’re really cool. Would you consider going on a date with someone like me who has been out of the game for such a long time? Would my “newness” be a turn off to you because I obviously don’t plan on getting serious with anyone really fast, but at the same time, I’m not a player (do people even use that word anymore?) I’m just “new,” I guess. And I kind of feel like an idiot, but at least I’m an idiot who can admit it.

So…Dear Reader(s), let’s get to it. These, of course, are my preferences, but I think I’m speaking for a lot of my fellow single Young Olds — if you disagree, by all means, chime in!

For my pal (who I’ll call Newbie), let’s break down his message in a few parts.

Part I — to chat or not to chat? I’ve written this before and I’ll say it again. I don’t like a lot of chat before I go on a first date. I definitely subscribe to what @nikoeman, aka the creator of “The Daddy Academy,” says is his method of communicating ahead of a first date — it’s direct; it leaves a little bit of mystery; and it doesn’t set you up to feel like you know too much about this person ahead of meeting. And that allows you an opportunity to ask questions and get to know your date organically. Too much chitchat ahead of a date is the wrong kind of build-up, IMO. Here’s Niko on this topic — also, is he the most adorable little dumpling or what?! I’m sure he’s 12, or something, but he speaks the truth.

nikoeman

A post shared by @nikoeman

Personally, when I was dating online — and we’ll get back to this topic, because it’s something I’m considering now, how I am going to start dating again* — if I connected with someone I was interested in meeting, I’d tell him that I felt like messaging on an app was clunky (it is) and then I’d give him my number.

I always took it as a really good sign if that person sent me a quick text right away, like, “Hey, this is Peter from Bumble” or whatever, because I knew he was prioritizing getting to know me a bit better and/or getting his number in front of me pronto. And after one or two text exchanges that DISTINCTLY DO NOT GET SEXY, if he hasn’t offered up a plan to meet in person, I’m able to say, “So…seems like we have lots to chat about. Coffee? Cocktail? Let me know. I’m avail over the next week or so.”

Getting down to brass tacks on this ^^^ makes a lot of sense to me. First, because we shouldn’t be endlessly texting, discussing what we had for breakfast, exchanging niceties about the weather. That’s OK We’re Dating, AKA, “how’s your day?” talk. Instead, this is me saying “I’d like to go out with you.” And since Newbie is ostensibly reading this, if you and I were chatting, you could then make your move, since I’ve given you more than tacit permission to approach me.

The other reason that brass tacks (maybe brass balls?) make sense to me is because if the guy does NOT ask me out for date in the immediate future, I assume he is just going to waste my time, and I’ll just stop responding. That could look something like this, Newbie:

Me: “So this is nice. Should we meet up for a coffee or a cocktail”

Him: “Who wouldn’t want to meet up with you?”

Me: Ok, I’ll put a “heart” on that comment (I am rolling my eyes) - but still waiting to see if he suggests a date.

Him: “Are you watching the new Jon Hamm thing on Apple TV? It’s really great.”

Me: “I’ll check it out.” And then go silent. Because, until he makes a move, or follows my lead to make a date, I have nothing more to say.

So if Mr. Hammalamadingdong pings me again and doesn’t ask me out, I’d just ignore him and move along. That’s NOT ghosting him, by the way, per the take-no-shit dating coach Sabrina Zohar. I don’t know Hambone, so all I’m doing is protecting my own headspace from someone who could be wasting my time. But believe me when I tell you, I’m pretty sure that Hammie will ping me again if he thinks I’m ignoring him. If it’s an invitation to go out, good. If it’s more blah blah blah, I’ll ignore the text. Then hopefully, he’ll just move along too.

So, Newbie, don’t bite the big Hamm Sandwich! You meet a woman online? Ask her on a date soon after you connect (assuming you live in proximity to each other etc.). My rule of thumb — if we’ve matched online, and have taken that messaging off the app and onto texting, my match needs to ask me out on a date within a week, and preferably, have one actual phone call with me, during which time, they also could ask me out, or reiterate that they’re looking forward to meeting in person. Otherwise, you get caught in the maddening time suck of “Oh, you loved Madness too back in the day? What was your favorite MTV video?” et al.

In summary: More than a week of “me too!” chat? No thanks.

Couple more things to add to what I just wrote:

• If you’ve met a potential date NOT online, but in the wild, I’ll assume you did some chatting when you first locked eyes. So perhaps you have more rapport going into this, since you’ve already been physically in front of each other. Still, ask her out for a real date sooner than later. “I’m so glad our paths crossed last night. Can they cross again next week? Wanna go back to the tavern for a proper drink, or can I turn you on to my other favorite place down the street?”

• See up where I wrote that I expect our early pre-date chat to include ZERO sexy chat? Newbie, I suspect that’s not your game plan, but for those men who are a tiny bit saucier, who engage with a woman online and think it’s OK to make a comment on how she looks in her bathing suit, or similar, NO NO NO. The Lady In Question has posted a full body shot of her wearing a bikini on her dating profile, because everyone knows that full body shots are a good move and she’s proud of how she looks. Fine. You can tell her that she’s clearly a stunning woman who must take good care of herself. You can ask her where she was sunning herself in the photo. Or you can make a comment about how adorable she looks with freckles, but that’s it. “Is that a string bikini? Because if it is, I’ve got great fingers for untying it” (TRUE STORY; some guy said that to me), ugh, NO.

  • AND…this is particularly personal to me, because, ahem, I write a dating, love, and sex column here and you’re reading it right now, so here goes. Just because you know that about me does not give you — a stranger— the right to speak to me in a way that seems overly forward. When I was on Bumble, I had a photo of me in bed, with my dog, in flannel pajamas, along with the answer to a prompt that read “I guarantee you that…” and I wrote something that I felt conveyed my more sensuous side, and showed that I was cheeky, within reason. I wanted any potential dates to know that I appreciated that part of me, even though I was middle-aged, and that I wasn’t afraid to show myself wearing pajamas with zero makeup. That photo actually weeded out some real douchebags, who wanted to know if I ever took off my pajamas, or whatever. Newsflash: it’s not an invitation to ask me if I’m DTF. It’s me saying I like being in bed and if you’re lucky, maybe I’ll invite you to join me here. Period.

    It’s also one of my favorite photos of me, actually (one of my partners had it framed; he loved it so much).

    

I think we covered how fast to ask out a woman that you’ve met online, right? Let’s go on to Newbie’s next question. Part II: where to go?

I like a walk, don’t you? Especially this time of year and especially if you can entice your date to meet you somewhere they’ve never been before. My 2nd date with my former partner B. was his favorite stroll around Astoria, Queens, including Astoria Park, and I was ENCHANTED. My 1st date with my former partner S. started out as a coffee and since sparks were flying, progressed to me showing him around the far East Village, my old stomping grounds, and I loved seeing it through his eyes. So, I’d say a walk is a safe bet BUT an even safer bet is a coffee (or a cocktail — ONE cocktail only) in a locale that could lead to a walk after the last sip was supped. Or get your coffee to go and stroll. A big nature walk — and I’ve done those — can sometimes be a bust if you and your date don’t gel and then you have to either suck it up or leave. I left, remember this one? I wasn’t impolite, but I wasn’t going to spend an hour with that guy either. Newbie, pick a small park or a pretty neighborhood with quiet streets. Have a good coffee bar in mind, or a cocktail bar that has popcorn or small snacks and even if you’re having a great time, only one cocktail, OK? It’s just the first date…relax, shaken or stirred can come later.

It sort of goes without saying that YES, NEWBIE, YES, YOU SHOULD ASK HER OUT.

Part III: Listen, I’m a fully actualized, completely self-sufficient woman who makes her own money, pays her own way, and can do almost anything she wants without any help. That said, I love it when someone asks me on a date and makes the plans for us. I. LOVE. IT. Asking someone out is a simple and easy way to show initiative, creativity, and interest. You do not have to ask her to go somewhere expensive or extravagant, just plan a nice hour or so. And if you’re not feeling creative, ask a friend to recommend some options — don’t toss it back at your date. It’s way less fun to hear, “I’m out of the loop. Where do you think we should go?”

Finally, regarding what Newbie asked about “someone like me” going on a date with “someone like him.”

PART IV: I’D LOVE TO GO ON A DATE WITH YOU. Are you kidding?!

Well, hold up, because, actually I don’t know my Newbie reader other than via his kind message and I think he doesn’t live on the East Coast, so for that reason alone, we’re probably not a match (and while I don’t mind dating someone out-of-area, there are limits, and, for that matter, shout out to my smartass beautiful friend Silvia who recently remarked about a former relationship and the lazy nature of that ex, “Oh, right, I forgot, Rhode Island is one of those pesky states where none of the roads lead out to other places. THAT’S why you always went up to see him!”)

Just because I have experience in Young Old dating doesn’t mean I’d turn up my nose at a newbie, ok, Newbie? Here are the quickie commandments of dating after you’ve been out of rotation for a while:

• Keep the chat about your former marriage or relationship fairly brief to begin. There is time to unpack all of that later. And for that matter…

  • If you don’t like your ex, probably best to work through as much of that as possible before you start dating. Personally, I see it as an ENORMOUS red flag when someone hates their ex. You don’t have to looooooove your ex, but a lot of venom? Nope, you’re not ready to date. I should’ve kept this rule more in mind with my last boyfriend, who was years past his divorce and yet still very prickly with his ex-wife. Turns out, I liked her A LOT when I met her. Turns out, that was def. not his best look, when he bashed her.

• If you’ve not been on a ton of dates, you can listen and learn a lot from someone who has been single for a longer period of time. Don’t be afraid to ask questions in the form of an affirmation, or a compliment, like, “Hey, I’m having a great time getting to know you. This is way less weird than I thought it would be. How does it feel to you?”

• Texting to check if they’ve gotten home OK? Lovely!

• Texting the next day to say you had a nice time and would love another date? LOVELY. That ridiculous “waiting game”? Yeah, ridiculous.

  • Likewise, I often text that I had a great time and thanks for spending some with me. It opens the door for another meetup, in case there was any doubt in my date’s mind.

    • And conversely, it’s really OK to text, “Hey, I had a nice time. I’m not feeling like we’re a match, so I wish you the best” is also fine. I’ve done that and I’ve received that text as well. All good.

*Towards the top of this post, I mentioned that as I start to consider how I’m going to date, I haven’t ruled out going back online, but neither have I made any moves to build a profile again. I’m kind of moving about the cabin rather slowly, since I’m relishing this time alone in a major way. I had this thought today. I want to start rewatching “The Sopranos” — that’s six seasons, 86 hour-long episodes. I’m PRETENDING that between queueing up the pilot and listening to THAT Journey song which wraps the whole thing, I’ll have figured out what to do next. In the meantime, don’t YOU stop believin' Newbie. You can do it. Godspeed xoxox