Dating Tips and Tricks

As a hetrosexual male in his mid-20s, I’ve gone on a few dates with women in my time. Some of these experiences have been good, though many have been bad. Likewise, I’ve been around many other individuals (both male and female, independent of their sexual orientation) who have also decided that going on a date was a good idea at one time or another.

Frankly, I find the concept of dating to be ridiculous, however I can see why some people find an appeal to it. Dating allows a person to seek out a potential life partner without making any long-term commitments such as seeing the other person ever again((Unless you want to)). In many cases, dates (particularly first dates) include awkward conversation with someone you’ve never met before. I promise you, their interest level in your story about being a drummer in an indie-country band is on par with your interest when they start talking about how their pet chihuahua fits in their Coach purse((If I ever heard that conversation taking place at a restaurant in real life, I’d consider self-lobotomy)).

That said, there’s plenty that I’ve learned in my dating past that I’d like to share with all of you. Some of these items may not be applicable to your personal situation, however we all know someone (a brother, a niece, a cousin, Vivette from The Lusty Leopard Club down the street) who could benefit from the following advice. Feel free to leave comments adding your own thoughts.

  • The best form of birth control is not abstinence. It’s dating a girl with a father who is a 6’7″, 450 pound ex-cop who has night terrors from his time in the Gulf War((Also ranking above abstinence? Literally, nothing. In practice, pretty much everything.)).
  • Being stood up on a date isn’t the worst thing in the world. Now you have time to do something constructive, like yoga, Sudoku, or masturbation.
  • Always ask for ID. Always. If possible, go to a place that requires you to produce ID to get in/consume alcohol.
  • Online dating sites aren’t as filled with creepers as you may think. I would encourage singles to try their luck there if traditional dating attempts have failed.
  • Avoid discussing politics, religion, or Israel on the first date. Unless your first date is in a Fox News studio((You know there’s someone out there who would think this is the perfect first date)).
  • If a girl hits you because “it would be fun to see a girl hit a guy for once”, she’s not the girl for you. Or anyone((This actually happened to me. More details to come in a future post.)).
  • Gentlemen — always offer to drive if any part of your date requires travel.
  • Learn what you don’t want in a partner early on. This will help you weed out bad first dates before committing to a second date.
  • Communication is key. A simple misunderstanding often turns a calm first date at a park to turn into a trip to a dark basement filled with occult flags, a giant black dildo, and Renaissance Fair regalia((Sadly, this also happened.)).
  • If you meet somewhere for your date, ask your date how long it took them to get there. If their time is more than three times what yours was, there’s a good chance this will be your only date.
  • There is a distinct difference between city people, country people, and suburban people. Learn which one you are and which category you want to belong to.
  • Shower before your date. Even if you plan on showering with your date at some point that night((Related note, guys: Trim your beard/mustache before a date if you’re not clean shaven. Facial hair is fine for a date, but look presentable.)).
  • Ladies — Beware a man who wears a three-piece suit on any first date that isn’t a black-tie affair.
  • Gentlemen — Beware a smooth-talking redhead in a dress of any length.
  • The larger the cross necklace someone is wearing (regardless of their gender), the less likely it is they go to church.
  • If your date asks you to call them by a nickname because it’s what their ex-significant other called them, bail. Quickly.((Especially if said nickname sounds like something an overly affectionate aunt would call an annoyed tween.))
  • Unless it’s obscenely hot out, wear layers. It gives you something to give to your date if they’re cold.
  • Google your date first. Even blind dates.
  • When in doubt, throw everything I’ve said out the window and just roll with it…except for the asking for ID part((Seriously though. Ask for ID)).

Front Page Image credit crises_crs via Flickr. Used under a Creative Commons License.


  1. Christa Lei says:

    I’d like to add:
    If a sexual encounter is imminent, make sure you always have a nail clipper or trimmer on hand. You’ll never go wrong.

    If a guy introduces a fetish to you anytime during the first date, make sure you have an out because you’re going to need to hightail it out of there ASAP.

    I feel really terribly that most of my experiences involve sexual activity, but I feel like dates go horribly awry once you introduce that factor in anyway– making for some of the funniest (in the most schadenfreude way possible) dates I’ve ever had.

    • Tim says:

      I feel like if anyone introduces a fetish, you need to have an out. With that said, how many people are introducing fetishes on a first date (serious question)?

      • Christa Lei says:

        I’m OK with certain fetishes. I mean, over the course of a relationship I’m sure people will introduce theirs at one point or another. I’m not down with all of them, but it’s fun to be open. That being said, I think always have an out is a good rule.

        And trust me, while I’ve met one of those people who introduces his fetishes on a first date– I’m sure he’s still single. Ironically, when I looked at his OKCupid profile later on, it mentioned that he didn’t have such a fetish and I laughed.

        • Tim says:

          This comment got me thinking — what things would I absolutely need to know about someone on a first date. Beyond obvious things like name, really the only two things I’d need to know are:

          1. Have you killed anyone?
          2. What is your religion?

          The first one is for my own safety (though after a particularly bad dating experience, I then googled everyone I went on a date with), while the second is just morbid curiosity, not to mention to hopefully help avoid massive relationship fights down the line.

          • Christa Lei says:

            I think I have the same two questions, but expanding off of #1, I usually see if they have the ability to kill me hahaha. I also went through a thorough social media and google search (I don’t know why people don’t realise they CAN do this. It keeps you safe?) I google-stalked my current boyfriend and I found it funny to try to keep things that I had already learned from him on our first date. He knows that I Google-stalked him now though, so I guess it worked out in my favor?

          • Tim says:

            I think there’s just a stigma that goes along with googling your date. Do it a little bit and you’re being safe/covering your bases. Do it a lot and you’re in line to get a restraining order.

          • I had a guy from OK Cupid suddenly start commenting all over my blog back when my mom and aunt were the only people who read it. I asked him how he found it and he told me he saw my profile on OK Cupid and found me.

            I didn’t use my real name, mention my blog, link to any social media, or share any contact information on OK Cupid. He also never messaged me on there–just saw my profile and decided to stalk me.

            One of the creepiest experiences of my life, no joke. I still have no idea how he found me. I blocked him and crossed my fingers hoping that he would give up. Which he did, thankfully.

            So yes, there’s such a thing as too much Googling your date. That’s it, right there.

          • Christa Lei says:

            With the advent of Google Image Search’s “search by dragging an image” feature, I’ve realised that stalking is MUCH easier– especially if the person uses the image a LOT. While I don’t think I would go as far as commenting all over the blog, googling someone has proven to be pretty helpful. For instance, I ended up reading a guy that I dated for awhile’s blog and realised just how deep his baggage and issues could go.

            But yes, that’s the ONLY reason why I’d be wary of Google searching your date ahead of time. Things like that (commenting all over the blog, etc.) are extremely scary and could put out the wrong image ahead of time. The sketchiest part about your story is that he wouldn’t message you… like why not? You’re already inserting yourself into my life that way. Did he think commenting on your blog would make the meet more organic or something?

      • Um. A lot. And yes, you need to have an out, even if it’s just “I’m really not into that” and then a super rude exit. Because seriously, red flag.

        Most people have them. I certainly have my share. But I absolutely do not share them on the first date, because that comes across creepy and forward and too personal to me. It’s a red flag that this is a person who doesn’t respect social boundaries, at the very least, and is possibly a super-creep.

        • Tim says:

          I completely agree that most people have fetishes. With that said, I really can’t think of many (only one time is coming to mind) times where that has come up on a first date. Maybe that’s because of the lack of times I was in a sexual situation on a first date? I don’t know.

  2. Kat Argo says:

    “Avoid discussing politics, religion, or Israel on the first date. Unless your first date is in a Fox News studio”

    I like to get that out of the way pretty much immediately. It doesn’t matter to me so much WHAT they believe, but whether or not they came to it logically or if they’re doing it just to piss off mommy, daddy or society at large. Also, if they’re offended by us having differing opinions, there will be no second date.

    • Tim says:

      I may have to go back and make an adjustment to that specific line because of your comment/a thought I had. There were very few things that disqualified people from getting a second date with me, but being someone who was not open to hearing/considering the opinions of others (no matter what they were) was one of those things. Frankly that line was in there because I had more than one first date where said date tried to force their opinions on at least one of those three topics on me. None of them ended well.

      • Kat Argo says:

        I like to believe it’s yanking the bandaid. Politics, religion, international relations is my life. I talk to enemies all the time. I can’t be with someone who is so embedded in their beliefs that each time I try to cross to the other side, they’re calling me horrid names or unable to understand why I think understanding both sides are different.

        Actually, on a few dates, if that comes up, I shut the date down, tell him thanks for his time, pay my part of the tab and go.

        • Tim says:

          The only time I’ve ever walked out on a date was when I got punched in the face because the girl “wanted to see what it would be like for a girl to hit a guy for once”. I feel like your scenario comes up far more commonly than mine though.

          • Kat Argo says:

            Okay, I laughed. I’m sorry.

            I wish I could girl power and say “You probably deserved it”, but knowing you… you didn’t. I’m sorry. Was she a nut job?

          • Tim says:

            The date lasted maybe 10 minutes, so I’m not 100% sure if she was. That said, considering that interaction, I feel it’s a fairly safe bet that either A. she was abused in a previous relationship (which would just be sad) or B. she was a nut job (which I find far more likely)

        • I have to agree. I tend to make it clear where I stand on politics, religion, feminism, veganism and the environment on the first date. Frankly, if someone doesn’t respect where I stand on any of those issues–even if they don’t fully agree–that’s a pretty automatic turn off for me.

          It helps that people have always asked what I “do” and it’s easy to just mention my blog and what it’s about somewhere in the answer. It makes it pretty clear where I stand without it sounding like I’m coming in all charged up. I also have blue hair, dress like a hippie, have buttons and patches all over my bag that make a lot of my stances pretty clear, and eat vegan (eating is a pretty common thing on first dates). Honestly most people who don’t like where I stand never try with me in the first place.

          Obviously I haven’t dated in a couple years since Tyler and I have been married. But if I ever date again, it will be right back to the same thing. I don’t have the time or the patience to give to people who can’t handle me or what I’m all about.

  3. Brittany says:

    I kind of really hope there is a blog post about #6, because that sounds super interesting.

    I agree about the politics & religion issues. Mention it, sure, but a thorough discussion would be a huge turn off. I’m more likely to be interested in the type of person you are and the general viewpoints before we discuss details.

    The layers are a good idea- as a female who is always cold, I approve. And the cross comment is probably true (mine is small-ish which I guess correlates as I go more than most).

    • Tim says:

      I actually talked about that one in the comments section a bit further up. Take a look at the chain between me and Kat Argo for further explanation.

      As someone who is always way too hot, I wear layers to allow myself the capability to not sweat like a pig. I’ve yet to find a climate that makes me consistently cold, while everywhere I’ve lived (even Ohio) has made me consistently hot.

  4. I’ve definitely never asked a man for ID on a date. But then…I’ve met 95% of them at pubs on the first date, which at the time usually meant they were my age or older. I did most of my dating in the year I was 21. Also in this society women have to be way less careful than men about getting tricked into anything statutory–partly because women aren’t judged as harshly for it, and partly because boys who are too young to be legal are pimply and awkward and can’t pretend to be older like girls can.

    Cross necklace thing: TRUE.

    And also I agree, internet dating is not actually the worst thing in the world, especially if you are a man and you actually receive a message from a woman (rare, and a good sign) or if you’re a woman and you feel okay wading through an ocean of messages that include dick pics and/or “ur sexy lets fuck” to get to the good ones (and are willing to be the woman who messages the man). I met a couple of really legitimately awesome people through OK Cupid.

    There are a lot of intriguing references here that sound like they lead to great stories. Stories which I think you should share with the audience. Just sayin’.

    • Tim says:

      The ID thing is for EXACTLY why you described. Statutory situations are really one of the fewer situations in society that are far more unfair to men than women (the only others I can think of are the stigmas towards early childhood teachers and the fashion world…not many, obviously). It’s harder for guys to tell if a girl is underage because women mature much faster than guys. Granted, under circumstances like you mentioned, asking for ID may not be as needed. Still never hurts though.

      I’m considering doing a dating-related post in the near future, likely focusing on online dating rather than my dating stories. That said, I may well write that up in the future too.

      • You should. It’s a really interesting topic. And while it absolutely is more unfair to men–like, super unfair–it’s actually something that’s addressed by feminism. It’s just one more result of considering women to be weaker…we treat them like delicate victims and ignore the plights of young men in the same situation. It’s so backward. And one more way that a patriarchal system hurts men too.

        I’d be very interested in a post about online dating too!!!

  5. Lucy Lees says:

    This is great 🙂 I’m currently in the process of dating (well, trying) after a bad break-up. I think that’s making it harder at times, but I have had my fair share of good and bad dates. Definitely agree that a google search is vital; gives you an edge on what can be an awkward first date!
    Life inside the Locket

    • Tim says:

      I’d strongly encourage you to read through my dating horror stories post that I wrote a couple of weeks later. If nothing else, this will help you to realize why I made some of the recommendations that I did.

      Dating sucks. It sucks even worse after a bad breakup, so sorry that you have to deal with that. With that said, I hope that everything works out for you.

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