Ask Dr. Nerdlove

How Do I Start Dating Again?

DEAR DR. NERDLOVE: I am much older than your typical reader but I really like the advice you give. I am getting back into dating at 51 and I really think I don’t know what the hell I am doing. I was married for 13 years with him for 15. I took a while to get my life together after the divorce, and I had one relationship for about six months since. Before my marriage I lived with somebody and mostly had long term relationships so I have not really “dated” since my early to mid 20’s.

I feel like the ground has shifted dramatically and that I am a massive prude and people are all out having threesomes and anal sex and watching porn and my dating expectations are probably very retro. I understand the basics, don’t talk about exes, don’t spill all your dirty secrets before you know somebody, don’t jump into instant emotional Niagara Falls. I am not looking to bag my soulmate or find a husband, i just thought I should stretch myself a bit and it would be nice to meet somebody to see regularly to catch a movie with or dinner or music and even sex. But I do feel like an alien from another planet. Everything is so casual these days and I struggle a bit with the ambiguity of it all. How do I adjust to the new world of dating and actually enjoy it while remaining true to myself. In short, how do I date when hooking up/casual sex is not exactly my comfort zone?

Stranger from an Old School Planet.

DEAR STRANGER FROM AN OLD SCHOOL PLANET: I realize it feels like you’ve been woken up from cryogenic stasis and now you’re in this strange world where people are melding their genes with aliens’ and we’re all eating caribou eyes and extinct cultures are being brought back in carefully controlled reservations but seriously: dating is still pretty much the same as it was 30 years ago. Social mores mean that more people are doing openly what others did in secret and we now have labels for things that previously went unsaid, but people are just people and dating is still dating. Some folks have lots of crazy sex. Some people don’t. Some people are serial monogamists while others play the field. Some folks meet their partners through friends, through blind dates, through personal ads, at work or at bars. Sometimes it may look a little different – Tinder and OKCupid have replaced the traditional personal ads – but at it’s core, it’s all the same as it was. There’s nothing new under the sun.

And you, Stranger, don’t have to do anything that you’re not comfortable with. You are perfectly within your rights to date the way you want, in ways that make you feel comfortable. The biggest thing that’s changed over time – one of the best things, in my opinion – is that we’re all increasingly free to look for the kind of relationships we want instead of trying to conform to a narrow and restrictive definition. And believe me, despite how it may feel at times, there are plenty of people who want what you want: something simple, comfortable and companionable.

The key is – as with most relationship issues – that you have to be willing to ask for it. Ambiguity tends to happen because people let it happen. Some people are afraid to be the first to try to put a label on things for fear of tipping their hand or coming across as too eager or desperate. Others like to keep things ambiguous because they want to use that uncertainty in order to prey on other people’s anxieties. But the fact of the matter is: you’ve got nothing to prove and, honestly, nothing to lose. Be clear and up front about what you want and what you don’t want. Be clear about what you’re looking for. Having strong boundaries – not wanting casual sex, for example – will chase off some folks and that’s fine. Those are people you’re not compatible with in the first place and the sooner you find that out, the better off you’ll be; you don’t want to waste time with people who don’t want what you want too.

And believe me: there’re people out there who’re in the same boat as you. They’re a little older, a little more mature, a little hesitant to step back into the dating world because it all feels so strange and different. But I promise you: it’s not as strange and mystifying as it seems.  You know what you’re doing, you’re just a little rusty. Just remember: take things at slowly and at your own pace. You don’t need to leap back in all at once; you can dip your toe in until you’re ready to wade in a little further.

Good luck.

DEAR DR. NERDLOVE: So I’m currently enjoying much more success than I ever have, hell in this past year I’ve been on more first dates this past year than I have my entire life (for reference: got married young, not necessarily the best decision)! I have more friends, get out and do new thing, etc. But I’m still trying to get to be the best I can be.

Also for reference: I work nightshift; it makes it hard to get out and meet new people (not impossible though!). Most of my date have been from online.

But the biggest reason I’m emailing you is because of the last woman I went out with. Actually, she ended up messaging me first online! We went out about a week later to a local barcade. Had a great time in my opinion, and ended the date with a kiss.

The second date ended up being about 5 days later, on a Sunday. She seemed a little stiff, and when I asked she told me she was just tired. So I was just being my normal, goofy self. We went to lunch and then to the Ripley’s museum downtown. At the end I was suggesting a group dance lesson for the next date

Fast forward two days later, I finally found a good place to go, and I texted her about it. She messages me back saying she wasn’t feeling it. At this point I’m a little perplexed by this (it seemed like we had a good time, and yes I had been trying to pay attention to her body language to calibrate myself during that date), so I ask to talk to her after thinking a little bit about it.

I basically said that “Hey, you know I think I didn’t let an emotional bond fully form, or express myself enough, and it stopped anything from happening, and I’d like another shot.” (Note: I made sure not to come across as begging. If she doesn’t want to date me I can’t force her). She responded by saying the big thing was the goofiness. It was too much. And her answer was “can I have some time to think about it.”

I contacted one of my close friends 2 days later and she said I kinda could be that way. And that we had never had a real serious conversation. It also made me realize a lot of my friends/connections are really light, there were only three main people I could think of that I would have felt comfortable asking about this!

And my question here is: can one be too goofy/funny/etc? And even if it is, I’m not necessarily looking to lose it. But maybe learn a time & place? Or to weave it with a conversation better? And any exercises/tips to be more mindful of this?

Come to think of it, I asked a lot about her (without over-questioning) of questions in the beginning when we first started chatted, then when we actually met up? Not so much. And I know asking questions is a good way of showing interest, maybe I need to do that more?

Why So Serious?

DEAR WHY SO SERIOUS: Straight talk my dude: you’re turning people off with your constant comedy routine. Humor may be attractive and women may love a guy who can make them laugh, but there needs to be some substance too.

On a strictly practical level, being continually “on” is going to make you less funny . Part of what’s important about humor is timing. Much like physical chemistry and sexual tension, you can’t just build and build and build. You have to have a release, a moment to breathe and recover and regain your equilibrium. Otherwise, all that happens is that people get overloaded and numb and check out completely. This is why comedic movies aren’t just non-stop slapstick affairs; they build to a crescendo, release, then let things level off before building again.

But you’re shooting yourself in the foot on an emotional level too.

If you’re just constantly cracking jokes and being goofy, then you’re not giving people a chance to actually connect with you. It can be exhausting trying to talk to somebody who does nothing but drop bon mots and witty quips because, frankly, you don’t feel like you’re on a date so much as being dragooned into being part of somebody’s performance.

In your case, your dates are trying and trying and trying to make a connection, to get to know who you actually are when you’re not being Mr. Entertainer and all you’re doing is just using them as an opportunity to make more jokes. And after a while it starts to feel like the joke’s on them. Small wonder they’re not feeling it with you; there’s no chance for a spark to grow because you’re continually sucking all the air out of the room. As any comedian will tell you: you have to be willing to turn the comedy off at some point and just be real. Let your authentic self show through instead of continually deflecting with humor. If you’re going to be jokey and quippy, then dial it back. You can still be funny and goofy and banter with your date, but you have to space it out and be serious far more than you already are. Treat humor like a spice, not the main ingredient and you’ll do better.

Good luck.

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