The Goal-Less Way to Enjoy Dating - Justin Lioi, LCSW - Brooklyn, NY

First date jitters. Excitement in the pit of your stomach. Intrigued by the new person who could become your life long partner… Are you too jaded to feel this anymore have you stopped being able to enjoy dating?

Stop Shopping

I remember in college someone told me that the women were “husband shopping.” I needed it explained to me because it just seemed so “missing the boat.” Why are we calling it that? Why is that ok?

Men “shop” too. Actually, these days I hear of more people say they are shopping for the father/mother of their children. It’s as if they’re not even thinking of who would be the best match for them, but for their unconceived babies.

No wonder they’re struggling to enjoy dating.

I’m not going to deny that while living in the moment we still need to look toward the future. There are biological imperatives when it comes to having children (and even though men can have child way into their golden years it is less risky to be working with younger sperm.) But if I’m just adding up the qualities of a person I can miss some real red flags. Not the flag of “serial killer” or something, but the flag that says, “this is not your match and you’re not giving yourself a chance to meet that match.”


There’s an old saw, “Life is a journey, not a destination”. It’s become hackneyed and the part of me that wants to mock anything on an inspirational poster is going to hate to admit this, but it’s true.

And it works when I remember to focus on it.

There are things to be goal-oriented about, but the stickiness of relationships isn’t one of them. I know someone who’s made an Excel spreadsheet in order to organize the data of their dates. I’m not saying this is a system that will always fail, but it keeps you in your head and finding a life partner should be about more than that.

Yes, keep your head about you when you’re dating. Don’t be led by only your emotions, of course (or any one part of your anatomy), but if you’re approaching dating like a math problem you’re most likely going to miss something.

Because relationships aren’t math. Yes, with online data we come up with all kinds of cool algorithms, but it needs to be put out there that maybe those brilliant matchmaking systems are stopping you from the chance meeting of the person you could really connect with. Someone whose data maybe doesn’t match your own, but is more intriguing and long-lasting.

Emily Dickinson (every man’s favorite poet when it comes to dating, right?) has a line, “I dwell in possibility” and that’s the feeling I want you to take on your date.

Tips to Enjoy Dating

If you are extremely, extremely nervous about dating and just beginning I would suggest scheduling as many dates as possible as close to each other as possible. A lunch and an after-work drink/coffee date in the same day. A Tuesday and Thursday evening date. This is to get you to a less nerve wracking place about the experience of dating. If you meet someone awesome, that’s great, I just want to get you out of your head right now and demystify the experience.

  • Make Each Date a Separate Experience: If you’ve been doing this a while and are jaded I say, do not schedule ten dates between now and Saturday night. You’ll have one foot out the door with all of them and will too easily dismiss them if there’s a hair out of place or they say the inevitable stupid thing that we all say on a first date. Once a week for you.
  • Meet Up Quickly: Don’t email for longer than one week, preferably only a handful of exchanges before you decide to get that latte. You want to avoid falling for the picture-on-a-website and the picture’s love of Game of Thrones instead of slowly falling for the living, breathing person whom (remember) you don’t yet know. I wouldn’t necessarily even talk to them on the phone. If you’re intrigued enough by the chatting, just get in a room together (a public room, though!)
  • Limit the Time: Make the date an hour. A first date shouldn’t go much longer than that. You’ll leave a five hour first date thinking too far ahead. Make that date number two.
  • Ask Questions (and Listen): Be incredibly focused on getting to know them instead of selling yourself. Let them get to know you by how interested you are in what they have to say, what their opinions are, what they’ve accomplished. When you’re asked a direct question, though, don’t be evasive. Be honest and feel free to be proud of what you’ve accomplished (without bragging.) Still, focus on getting to know them. You’ll figure out whether you want a date number two and you come across as a great listener—win-win.

You can enjoy dating even if you’ve been doing it for way too long—or restarting after the end of a relationship. It helps to not be fully in the “goal oriented” mindset that you might take on a career hunt, but a curious and intrigued demeanor in getting to know your date will go a long way to keeping you in the moment and, possibly, enjoying the simple process of getting to know someone whom you didn’t know before.

A lot of people struggle with not being able to get out of their own head or are banging their head with all the dating they’ve been doing. If you’d like to talk further please get in touch and we can schedule a 15-minute FREE phone consultation.

Justin Lioi, LCSW is a men’s mental health and relationship expert based in Brooklyn, NY (and online throughout New York State and internationally.) He received his degree from New York University and has been working in family and men’s counseling for over 10 years. Justin is on the Board of the National Association of Social Workers and writes a weekly column for the Good Men Project called Unmasking Masculinity. He can be found on local and national podcasts talking about assertiveness, anger, self-compassion, all with the goal of becoming the man you want to be.