Dear Unexpectedly Single Men of a Mature Age: Notes about Dating….Again.

Caveat: Because my experience is with cis-gendered, hetro relationships, the assumptions and words I use reflect that. The hints may well apply across genders and orientations, but I don’t assume that’s true.

Dear Single Men of a Mature Age,

After years of having a partner, you’re footloose and fancy-free…possibly not by choice. Definitely with a couple decades of experience and baggage. And you have realized that there are only so many microwavable dinners you can stomach before you’d like company. Preferably not the same people you see at work or around the neighborhood.

Maybe a friend knows a nice single woman who you meet and click with, and you don’t have to eat meals alone as often. If that’s the case, this note is not for you. Instead of reading this, call her and say something thoughtful to her. You don’t know how lucky you are.

If you’re still reading, here are a few tips. If you haven’t been dating for a decade or two…or three..the world has changed. Unless you happen to get lucky by having a friend who knows a nice single woman, you probably need to change your approach and assumptions, too. Or do you have a fondness for microwave meals and watching the weather channel?

Not all of my tips may apply to you, but before you dismiss them, consider this: what you’ve been doing may not have worked as well as you wanted it to, or you would have stopped reading a couple paragraphs ago. You may have been thrown a hard curveball, and your current life is different than you expected it would be right now. Taking a few moments to think about new approaches might be called for.

  • First, know that you have baggage, expectations, and assumptions. Everyone does, and you’re not a starry-eyed teen just starting out, so you have more than you used to. Take the time to think about what those issues may be — if appropriate, with a therapist — and know that if you are successful at connecting with new people, you’ll find that you have even more baggage, expectations, and assumptions than you thought. That’s ok. That’s a sign you’ve had life experiences and you’re still growing.
  • Learn enough about technology to use a dating app and to text or message. (More about the dating app in a bit) Every mature woman I know texts a fair amount. They text to each other, to family, to arrange social/work/volunteer times. Get comfortable texting a hello and a quick thought — a whole conversation isn’t required, but texting and messaging are how people keep in touch. Even if you’d rather call or email, a quick text to say “good morning” is usually appreciated.
  • Use your words! Ask questions. Clarify, and be open to new ideas or ways of doing things. Find out if texting is appropriate or if they’re prefer you call. Let them know if you like it when they initiate contact, or if you’re from the school of thought that feels it’s too forward for a woman to hit the send button when you’re not expecting it. You’re allowed to have preferences and to express them, but having a discussion instead of issuing edicts (or worse, expecting her to “just know”) is how grown ups operate now.
  • Consider what you’re looking for. Do you mainly want a social companion, someone to go to the occasional event with, to watch movies or eat dinner with, no deep emotional ties or chemistry needed? There’s nothing wrong with that — and you might be surprised how many women would find that to be exactly the sort of relationship they would like. Are you hoping to find someone to marry — or at least intertwine lives somehow? It’s even fine to admit you’d like someone to cuddle (or more), but you don’t want a commitment. Even though situations can change, and you could be open to a combination of possibilities, think about what you are actually hoping to find. Be willing to have those conversations and have them sooner rather than later — especially if you have a strong preference. Don’t assume that every woman is looking for another husband. (I don’t know any over the age of 50 who are, in fact, but my sample size may be too small.)
  • Unless you have an extensive social network, using a dating app might be a good idea. It’s fine to put a picture or two of you a few years ago on your profile, but include one or two recent pictures, too. Have at least a couple pictures that are just you, not you and your kids or grandkids, or you and your ex (yes, I’ve seen that on profiles.) If you have hobbies, interests, or passions, share them. Put some thought into what you write on your profile so it attracts the sort of person you’re most likely to connect with.
  • If a profile hits your fancy, don’t message “hey beautiful.” Ask a question or comment on some info from their profile. Show that you read it and you’re not randomly messaging every female. And respond if someone messages you, even if the response you make is a polite “Thanks for noticing me, but I’m not interested.” Saying things like that on dating apps is acceptable.
  • And — -maybe most importantly — try not to ghost. Ghosting is just disappearing. You’ve been in touch, maybe even gone out a time or two, then….nothing. You realize you’re not interested, or that you aren’t ready to make new friends/have a relationship, or…whatever. Ghosting is not answering a text, not making a call, ignoring an email until it would be awkward to answer — those are all easy outs. If you realize that you’re not interested in continuing, say so. “I’ve had a good time, but I’ve realized that…” is a perfectly fine way to say you’re moving on. There are probably a hundred other ways to frame it. But be a grown up and say good bye, even if your only reason is the chemistry isn’t there. You don’t have to argue your position or earn the right to walk away — that’s your prerogative — but unless there’s a pressing reason to ghost, don’t. And if you feel as if a woman is ghosting you, ask. Be ready to accept whatever she says, but don’t sit there wondering.

I’m sure I’m missing crucial tips, especially for those of you who have been blindsided by a sudden divorce or death — I’m so sorry, but the world you’re waking up to isn’t the same as it was. Once you get your bearings, though, you may be surprised by the possibilities surrounding you.


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