Dating 101: This is Awkward


Q: Dear Randall, I’m such an awkward dater! It makes me uncomfortable to [make] small talk in new settings with people I don’t do very well with the expectation that we figure out if we “have a connection” or whatever. I just want to hang out, doing something that I would typically do on a frequent basis, and preferably surrounded with people I’m familiar with. That’s more accurate of who I am as a person, not throwing me into something that is outside my element with someone I don’t know well. It feels like “work”; is it normal to feel like going on a date is “work”? Maybe it’s because I’m an INFJ. I just want something more authentic and deeper, but the small talk kills me.

A: So… all of that makes sense.

It sounds like I’m also an “awkward dater” by that description! I’m also an INFJ and small talk bores me to no end. I find that I want to push right past all of those initial questions and get to know the person behind the presentation. Sometimes, people don’t know what to do with that and clam up, but most times, they open up and walk away shaking their head afterwards wondering how they made a best friend in under a half hour.

Which is to say… Yes. Dating is work because it’s not friendship. Friendship comes naturally, organically, without effort. There’s no pressure because your “friend” is a nuanced individual and you’re not pinning all these expectations to them — Should we marry? Do I want to have kids with them? Will they make me happy? Will I make them happy? Will they be faithful or embarrass me?

Dating is work. It’s pressure. And it needs to have tangible results. That’s what work is. You invest in that thing for more hours a day than you do reading for pleasure, talking with friends, etc. When the end-goal is “spending our lives together” and “this one person”, that’s a lot of pressure. ‘When you get married?” becomes a deadline. Kids become your “next project” and… friendship? Friendship, hanging out, “chilling” are not the same thing.


Here’s my thought: If you want to get to know someone first, “just want to hang out” and do things on your own terms? You’ll probably be friendzoned and (unintentionally?) friendzone them. You will never feel that “spark” because… they’re your friend, your buddy, like a brother, etc. You’re doing what you would do anyway (pause) by yourself (pause) alone (pause) or with “friends” (pause). Let that sink in for a second. There’s no novelty or innovation (which is also work, because it requires an effort on your part) and you’re not in the razzle-dazzle of a new circumstance, say a restaurant or a road trip somewhere to “feel” anything different or see them differently.

I’m not scolding or anything. In fact, I say all of this as someone who has done what you’re talking about and, ideally, would keep doing it. Love on my terms? Where there is a high degree of comfort and safety for me and you’re a new toy in the playpen, proving yourself for me to decide whether I want something with you? Who wouldn’t want that?

But playing the Devil’s Advocate here, doing all of that mutes the other person’s ability to peacock and (to be blunt) leverages things in such a way that they really have to do something drastic to make you see them as something more than a friend. They have to make a bigger, bolder investment than I do. And I’m safe because, hey! If I’m not digging it, I’m already doing the things I like – watching the movie I want, hanging out with friends, etc. – and what I would be doing anyway. For someone who is interested in you and wants to break off from the crowd, all of this is “romantically inhospitable.” But it’s not awkward.

Example: What you’re talking about works. “Just hanging out” is a real good way to get to know someone. No question. But I once dated a Ukrainian woman who had to take her top off and call me into the living room for me to go, “click Lightbulb. Oh. Oh! Hunh! She… actually wants to do something more here. She wants to do more than hang out.” And while I really enjoyed that, she said she felt she had to do that to get out of the “just hanging out” category. We had made out. We had done other things. We had gone for walks, talked, went shopping for shoes, but she said she felt like I wasn’t getting the signals that she wanted something more. That she was falling for me. So she had to take it further to get herself out of the category I had (unintentionally) put her in.


In hindsight, is it possible that the guys you’ve gone out with recently have been making big efforts and you either didn’t see them or felt turned off by them because they weren’t part of the world you’re comfortable in? Shut your impression of those guys down for a second, being turned off and so on. From their perspective, were they making “big” gestures to try and get you alone and create “hospitable” conditions for something more than friendship? To present themselves as something other than “just a friend” or someone who can get lost in the crowd of friends? I’m betting, from their perspective, that’s what they were trying to do.

However – again – I get it! As a fellow INFJ, maybe what’s happening is that you know you have the goods. No one can Bird of Paradise you. You can impress yourself, pay for a good meal, go see the movie you want, and keep yourself occupied. And, again as an INFJ, I know that this means you’re probably secure in who you are and your preferences. You’ve tried things. You’ve lived life. You’ve gone places. And you’re probably not going to be impressed that the restaurant they chose serves flaming marshmallows rather than marshmallow cream. Ooh. Wow. Yeah. Seen that a hundred times already. Really blew my mind here, chief. Nice restaurant choice. Can we go now? The game starts in an hour.

Guys, in general, don’t know what to do with that. Either they feel like they need to do big things and are confused when you already have plans, when you have your big girl panties on, when you have a great job that you love, and when you are surrounded by solid friends who give you the love and attention you need. A girl who doesn’t need a man to complete her life of consuming? Unthinkable! Or, second option, they hear you and see you and would be amazingly awesome for you, but feel they have to walk away because there’s no room in your life for them. You have what you want/need. No “reason” for them to stick around.

My mind keeps circling back to those times when dates stopped trying with me because they could tell I was bored. I had my stuff together (sorta) and they didn’t see how they fit into my life. In economic theory, this means you are aware of your value and won’t trade for lower-performing (i.e. superficial) goods until you have determined their worth on your own system of currency (inflation/deflation of value based on determinate of worth = observing them by “hanging out” or joining the things you are already doing). I think in some way, you are transposing their criticism (“I’m awkward”) for your authentic self valuation (“I’m a boss”).

That is, it doesn’t sound “awkward” that you want to sidestep “the big show” and get to know a person for who they really are. That sounds like being an adult. Wanting to know people and accept people based on “real data” rather than their “marketing” is a really healthy, wise, and mature decision when it comes to dating. I’ve dated women who promised a great many things and had a sexy image, but once we alone were boring and (worse) had the double-toxicity of being both uninformed and opinionated. Yuck! So major points to you for wanting something real. That’s not awkward. Maybe how you’re going about it is awkward. Like I said earlier, I have a tendency to want to cut through all the huff and puff, and that can be perceived as intimidating.

So, realistically, what will it take for you to let someone try with you? Even if they don’t succeed, do you want to allow people to try and impress you? My guess from your initial question is “No.” You’ve endured enough of the rodeo and have better things to do. So, again, realistically, what will it take to change your dating habits and let someone in?

It sounds like you need to change your venues and meet some new guys. See my next article, “Where to Meet People” (or as one friend called it today, “Where to pick up chicks and catch some dicks”).


But before I toss you off to the next article, maybe I should share one other option. Maybe it’s something more than just wanting more than a good show, or having your shit together and guys being intimidated by that (and being too dumb to hang out when you invite them into your world).

Maybe you’ve been hurt and want to go low-key for a while so there’s not this romantic atmosphere which can hurt later? You try to keep things low-key because if it’s “just hanging out”, you won’t get hurt again.

After my Great Heartbreak in 2010, the women I dated told me I was great, they were having fun, but ultimately I wasn’t emotionally available. I was still hurting from that and didn’t want to put all my cards on the table again and lose.

I think that’s actually a really good way to talk about it – like a card game. I had “lost” a lot in 2010. And I needed time to go earn some more chips before I sat back down at the table. I love a big game, I love going “all in” with high stakes. I love having a partner, the whole experience of giving my house and car keys to someone and welcoming them into my life, of them welcoming me into theirs. But for a long time after my Great Heartbreak, I had lost so much in such a big, public way that I simply didn’t have anything to give, trade on, or “play” with. I wanted a safe game. No risk. No real major winnings, but then again no major losses either. And as a result of that, I kept my cards close to my chest (didn’t really talk about myself a whole lot), placed low bets/wagers (“we’re just hanging out, we’re not dating”), and stayed at the tables and games that I knew would pay off (close friends, family, my books, etc.). I wanted the familiar to help me process but also keep me insulated and safe.

Coming back around to this bit about “the expectation that we figure out if we have a connection or whatever,” how will you figure that out? It won’t be when you’re “hanging out.” Hanging out for you at this point is really a first step to something more. You probably won’t know until someone takes their top off in the living room and you feel an immediate “Oh. Ohhhh!!!!” or you get out of that safe cubby you’re hiding in.

I guess what I’m saying is, I get it. You’ve been hurt so you’re wanting to play it safe and “just hang out” until you know they won’t hurt you. You want to do your own thing, be with friends, and if your potential-future-Mister fits with that? Then they’re invited. But what will a guy have to do at this point to get your attention, make a connection, get you out of your routine and comfort, to make themselves seem datable?

They’re going to ask you out, of course.

They’re going to do the mating dance, of course.

Most people don’t zip straight to the “something more authentic and deeper” thing like you and I might do. They’re going to either be in their own cave, or they’re going to try and find a neutral ground like a restaurant, a stand-up mic, an art show, helping them find a gift for their nana – something superficial and low-contact where you can both still walk away if there’s no “connection.” And that’s okay. Things don’t always have to be on your terms. Sometimes, it’s okay to give them some space to work their magic, try their tricks, and make an effort to impress you.

But it’s also okay to not be impressed by that. To end the date by saying, “I didn’t have a terrible time. Maybe next time, we just hang out – with or without other people – and keep seeing where this is going” because the pressure to decide whether you “had a connection” and now you’re going to get married and have kids and the 401K and put each other’s names on the insurance policies and (deep breath as a I have a panic attack)… is a lot of pressure. So give yourself, give your relationships, the permission to go out a few times and develop a connection. If you want that. See whether you feel anything after doing a few things privately and with friends, then go out a few more times to see what happens. But be clear with him that it takes you a little while and make sure he’s okay with that too. You don’t have to tell him your dating history or who hurt you and how. All you have to say is, “Hey, it takes me a while. This is who I am. I do better when I’m ____ or we do ___. Will you be okay with that? Giving me some time to figure it out?” and if he respects that, Yay! If not, then he’s rushing you (maybe for good reasons, maybe for not good reasons) but you’ll know right there it’s not a good fit and you can walk away without guilt or shame.

Anyway, stay tuned for the next part of the Dating 101 series, “Where to Meet People”, right here on Sexuality & the City!

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