Dating Again, in Your Mid-Life.

How to start dating again in midlife?

Staring down the road of dating after a long break can be pretty terrifying for most people. At your midlife, you may have some kids, a career, a full schedule, and maybe even a history of relationships not working out for one reason or another. You might think you have “too much baggage,” feel unattractive, or just plain out of energy. Then, there’s the matter of how to fit someone else into your already full life. All are valid concerns, but I encourage you to keep all that for later after you find someone. If those concerns still feel important after you start dating, revisit them then. Let your focus be first on just getting started.

So, how to get started? What is dating like now? Do I have to use the apps? Some people might tell you first to get a sense of what you’re looking for, envision a partner, and then look for that partner. But I’m a fan of people jumping in the deep end and getting some experience first. To know what you want, you need to have a new experience. And if you are considering dating in mid-life after a break, you need to get some practice. It’s like training for a marathon; you have to gradually build up the volume in your mileage before you can expect yourself to run an entire 26.2 miles. Well, the same would be true about dating. You need experience with people and small talk and deep talk and flirtation, in general, to feel into who you would like to invest in (note: you also never have to invest in monogamy and stop “dating” again if you don’t want to, but I won’t go there yet).

How do I meet people?

I suggest my clients get on the apps and start connecting ASAP. You don’t have to be on the apps, but it’s a great spot to tap into a pool of people who also have decided that they would like to date. It’s like walking into a bar, and everybody there is at the event because they’re single and ready to mingle. Your chances of finding somebody who would like to meet up are incredibly high. And yes, it’s true, there’s a lot of ghosting and general debauchery on the apps, which would be something to consider; now is the time to begin doing the excellent work of not taking other people’s actions personally. But you can have fun with this and keep it light in the beginning as you get to know people and let them get to know you.

However, one caveat I emphasize about the apps is to keep your messaging on the app short, sweet, and focused on the point: to get out into the world and meet up. Here is where you might want to know at least your “deal breakers” to do some initial sorting. If there are major red flags for you in your messaging, end the message as promptly as it began, and don’t waste your time. But don’t get too caught up in your imagination at this stage. If there aren’t any red flags, see what it’s like to go with it, and remember: practice makes progress.

How can I meet people off the apps?

If you are very against the apps, you will probably have a slower start and less of a field to practice in, but there are other great ways to meet people still! You just have to do a bit more thinking and strategizing.

If you want to meet somebody more “organically,” the same rules still apply; you will need to meet up and get to know people. However, without the apps acting like the digital bar full of people who are single and ready to meet, the “real world” is not this way. So, you want to start thinking about where people with the values and interests you like might be? What would the people you think you might like be doing? Perhaps they go to church? Or volunteer in your community? Or maybe they are lap swimmers at the county pool or the dog park? Consider: What do I like to do? What am I all about? Go there, do that, and start conversations with people you find interesting or are compelled to stand near or look at for longer than a couple of seconds.

And finally, let the people you are close to know you are open to a connection! And, simultaneously, let them know your deal breakers and boundaries. For example, perhaps you do not want to be bombarded by a blind date or set up with a particular single mutual friend. Make your boundaries clear. This might sound like, “Hey, I’m ready to start dating. I’m excited about the idea, but I’m also nervous. If you know or see anybody you think might be a good match for me, I would love to know about them. You can tell them about me too, but I would prefer you to give them my e-mail over my phone number. And I don’t want to get set up on a blind date or be surprised in any way.” If you feel comfortable and enjoy spontaneity, leave it open and let your friends and family act as your matchmakers! You can refine and rewrite your boundaries at any point based on your evolving comfort level.

What should I do on a first date?

Let’s throw out the dinner-as-a-first-date trope. And, please, whatever you do, do not go to a movie on a first date! These are perhaps the worst ways to get to know someone new. Go on a walk, grab a cup of coffee, or go to a local outdoor event. Do something you would naturally enjoy anyway, where you feel comfortable and can move around and share an experience. Anything that doesn’t involve sitting, staring, and interviewing each other as is done on a table service dinner date. Keep it bracketed regarding timing, too, like, “Let’s have coffee- I have 20 minutes.” Or suggest a walk on a well-known path that you know takes about 20-30 minutes from start to finish. This way, you have an easy out if things are terribly awkward, and even if they go well, you can keep the introduction short and sweet or extend the date. It’s always easier to extend a hang than to cut it short.

What should I talk about on a first date?

Hang on to this perspective: every conversation and every interaction is a learning experience for you. Please throw out: I must be interesting and likable. Pay attention…what do you notice about yourself when you are with this person? Is it hard for you to share about what you’re up to? What you’re into? Is it hard to wait your turn to talk? Are you finding yourself disappointed by the reality versus the expectation? Find your edges and use this experimental period as a gateway for self-growth. Because, after all, you’ve made it this far with yourself (and, hopefully, with your community having your back), you don’t need a partner; you want a partner – right? Trust this couples’ therapist, you want someone you can be yourself around, so take your time feeling and trying things out. Let go of canned conversation and neat presentation.

I met I would like to know more deeply, now what?

This is so exciting! Please let it be exciting and fun. Don’t go ruining it with overthinking. I know you wouldn’t do that, would you? I’m teasing…we all overthink and get way ahead of ourselves, but let’s keep in mind the spirit of this blog article: get to know people, let it happen, let it grow, and enjoy the process of bonding with humans. Take your time and sip all the sweetness from the bonding stage. Enjoy the fascinating process of revealing yourself to another and being let into another person’s world. If we take our time to let it grow, we get a sense of how we mesh with another person. There are also some built-in protections through “going slow”- you can notice if you slip into old and unhelpful patterns, and you can keep in touch with the reality of how you feel with the other before getting swept away by the delicious chemicals of early bonding. Most importantly, you can set healthy boundaries and expectations right away.

Now that you’ve met somebody that you’re interested in let them know. Let them know that you find them interesting, that you’d love to hang out more, or that you enjoy spending time together. And go after it. In this stage, people often start playing games to protect themselves because it’s scary to have your sights on someone, as it illuminates the fear of loss. But loss is inherent throughout any stage of life, even if we’re married, as you may know well. You’ve made it this far; if things go south, you will survive because you are resilient!

Be transparent and revealing. Lead the way in the relationship. If the feelings are there in the other person, your transparency will invite them to follow in step. And if their feelings are not there, it’ll be easy to spot a difference early on. It’s a win-win. This might be a scary stage, but don’t let fear drive you here because, remember, the long-term goal is to get to know somebody who meshes with who you are and fits into your life because at this stage, what the hell is the point otherwise?

And since you’re in midlife, you have other things going on. You have kids or a career, or maybe you enjoy your solitude and your routines, so have a conversation early on about your preferences regarding space, sex, and communication. Do you like texting conversations late at night? Do you hate texting and want only phone calls unless it’s regarding date coordination? Do you want to meet up on weekends only? Do you want to be monogamous or something else? How often and what kind of sex are you into? Think about the ways you enjoy interacting that make you feel alive and like yourself, and get honest about it right away. It could go something like, “I enjoy spending time with you, but I’m at my best when I’m out and about enjoying an activity together. Would you like to plan on going on walks together and coffee on Sunday mornings?” Or “I have a very full life, but I like you and think you’re really sexy. I would love to have sleepovers on Friday nights when my kids are at my partner’s house.”

Throw expectations and “relationship milestones” out the window. And HAVE FUN.

I am sure you’re starting to get a theme here. The question was, “How do I start dating in midlife?” And I haven’t been answering that question. Instead, I’m explaining how to start getting to know people- and yourself- to build the basis for dating in a more genuine way. And I wish we would talk about dating like this for any age and stage. It’s not about the end goal (i.e., dating, exclusive, friends with benefits, engagement, etc.). It’s about opening up to the process of getting to know people, expanding your self-knowledge, growing a thriving community base, and allowing something to grow from there that is enriching for you. We often don’t know what we want until we experience it, so we need to have plentiful experiences and to do that, we need to throw out the idea that the “end goal”, or labels, are all that important.

Remember to have fun, take it slow, and build new relationships intentionally as you experience them (not in the echo chamber of your mind!). You do not need a partner(s); you WANT a partner(s). Remember that and let the process of dating be about your self-growth and the expansion of your world to include another person or people. And if you do, I promise that dating again in midlife can be thrilling, fun, and even sexy.