How to Not Suck at First Dates

leia date

Ahhhhh, the dreaded first date!

Your palms are sweaty, your arm pits are sweaty… okay pretty much all of you is sweaty. Wandering into the unknown, your head explodes, imagining every possibility: Is this date gonna suck? Is it gonna be awesome? Is this going to be the person I spend the rest of my life with? What if this or that happens?

For so many Rebels I’ve talked to, trying to get healthy is closely related to our hopes of finding someone special to spend our lives with. It certainly influenced why I started getting healthy and has continued to play a role in my decision to exercise!

Having been on my fair share of both amazing and cringe-worthy first dates (way more of the second one than the first), I feel like I have a pretty firm grasp on how to kick ass at first dates.

No falsifying yourself… no being somebody you’re not. Instead, we’re just going to present ourselves in the best light so we have the best chance to make a real connection with somebody.

Here’s how to stop sucking at first dates and go in with confidence.

Where Does One GO On A First Date?

wine date

You may not think it, but where you go on your first date can have a HUGE but subtle impact on how things go. It can also be the difference between a real connection and a train wreck of an evening.

Let’s start by determining how you met each other: Was it through the internet or a dating app? Is he/she the friend of a friend? Did you meet at a bar, party, or use 20 seconds of courage to ask out that cute someone in line at the coffee shop?

This will dictate the type of first date you want to have. The point of the first date should be to determine if you have a connection with somebody (not fall in love right there).

1) IF YOU HAVEN’T MET THIS PERSON IN REAL LIFE YET:  My recommendation is to start with coffee, a drink, or something light hearted like meeting at a park. NOT dinner and NOT a movie. There’s nothing worse than learning within 5 minutes of meeting somebody that you’re not a good fit, only to have to sit through a three hour dinner or sit in awkward silence next to them at the movies. This is why I like drinks or coffee. If it’s going well, there’s an attraction and conversation is coming easily, you can order another. If not, you can politely decline another round, say you need to get going, and bow out gracefully, saving you both from an uncomfortable evening. If you aren’t sure what type of date to plan, err on the side of this category.

2) IF YOU HAVE ALREADY MET THIS PERSON IN REAL LIFE: Consider the above options, but also consider something a bit more adventurous if you already know this person and have talked about something you both enjoy (swing dancing, a museum), etc. If you know there might be some connection or shared interest, you have some extra room to venture out from the low stakes, playing-it-safe method above. A museum, rock climbing gym, a stroll in the park, or something a bit quirky that you know you both enjoy.

3) EITHER WAY, DO NOT FLAKE OUT: Be a person of your word – if you commit to a date, go on it. Don’t say yes, and then text them later and change plans and bail on it. If you don’t want to go out with somebody, POLITELY DECLINE FIRST. I don’t know why we think that saying yes only to say no later is better – it’s not and makes you a crappy person. Texting makes this pathetic practice an easy out. Aziz says it best:

Okay, so now that you know WHERE to go on your date, it’s time to get prepared for that date. You need a solid battle plan.



Like any great war or battle, most of the work is done before a date starts. No, I don’t mean stalk the person you’re going to date and know everything about them. In fact, I recommend not internet-stalking your date! It’s far better to get to know somebody from talking with them rather than pulling a: “so I read your Facebook page and looked through your photos, tell me about your trip to Guatemala in 2010! Also you looked nice in the red dress in March 2013.” What I really mean is making yourself a worthwhile first-date (and beyond) candidate!

Take care of your appearance: This starts by taking care of yourself physically – if you’re here reading NF you’re already taking steps down this path. Yeah, your mom says “beauty is only skin deep,” and “don’t judge a book by its cover.” HOWEVER, in reality we judge people every second of every day, and we are going to make a first impression (good, bad, or weird), on EVERYONE we meet. Might as well put our best foot forward and show our best side so the kick-ass parts of us (what’s inside DOES count) actually gets a chance to shine. Now, a huge part of this is…

Dress the part: Dress appropriately. When in doubt, go a bit too formal rather than a bit underdressed. It could be a sport coat for guys or a dress/skirt for women. Better to look a bit TOO stylish than like slightly on the slob side of things. T-shirt and flip flops is great for the beach, not for a date. Obviously this depends on the date you’re on (drinks vs. rock climbing), but take care of yourself.

Want to learn how to not dress like an idiot? Read this (our article on not dressing like an ass). A word to the wise for all: dousing yourself in axe body spray/cologne/perfume is not cool.

“But Steve my style is this nerdy t-shirt and these holy jeans, and I want to be me.” I hear you, but remember that this person is likely going to judge you instantly before you say a word, and if you want to have a chance to share your awesome, quirky personality, it has a better chance if it’s packaged with a solid outward appearance. Think comfortable and designed for your body type!

Be interesting: This gets better with practice, but you become way more interesting if you do more things than “I work at Innotech, and I like TV.” I can’t tell you how many dates I’ve been on with a woman who said “Well I go to work, and I love to watch Netflix.” Hard pass. No matter who you are and what you like to do, there is something more interesting about you than the last thing you queued up to watch.

DO NOT LIE TO SOUND COOLER. You CAN, however, learn how to present yourself in the best light that makes your story more interesting. Which person would you rather hang out with?

“I work in IT. I like Netflix. I sleep in on weekends. I drink a lot.”

“Well, I work in the technology division of my company, but I spend my free time hiking with my dog, Rebel. I’m trying to learn to play the guitar because it looks like fun. I just started planning a trip to Croatia because I want to check out Plitvice Lakes.”

Remember: You’re not bragging, but sharing the real you in an interesting way. Not just where you are now, but where you are now and where you want to go. This means not just the “I work here” nonsense. That’s boring and doesn’t define you. That’s a box that we’re taught to put ourselves in. Be better than the box.

Okay, we’re ready for the date!

What the Hell Do I Talk About?

“Steve! Help! I suck at conversation and I don’t know what questions to ask and I hate awkward silences. AH!”

The point of a date is to get to know somebody and see if you have a connection, so you want to create some back-and-forth (like a playful volley in tennis) in which you’re both asking questions of each other and answering their questions with more of your own.

These are the two extremes you want to avoid:

  • Avoid feeling like you are conducting an interview. In these less-than-optimal dates, every question got a one-word answer or two. If somebody is asking you a question, feel free to explain your response with a “here’s an answer, and here’s why. What about you?” This helps avoid the following:
  • Don’t let THEM ask all the questions. When I end up doing all the asking on a date, I learn a LOT about the other person (mostly that they’re selfish or unaware), and they learn next to nothing about me. And I leave those dates with the impression, “Wow, she went on forever and ever and never once asked me a return question.”

For us introverts, it can be tough, but memorizing a few fun questions can be really helpful in getting the conversation started. These are my go-to questions after we’re in the conversation a few minutes – the sooner I can get past the small talk stuff and REALLY learn about somebody, the better:

  • If you could wake up anywhere in the world tomorrow, where would it be?
  • If you could only eat one meal for the rest of your life, what would it be?
  • If you could have any superpower, what would it be?
  • What’s the best concert you’ve ever been to?
  • What’s your favorite guilty pleasure song?
  • If you could be the best in the world at one activity, what would it be?
  • What’s the most exciting thing that happened to you in the past week?

Notice in each of the questions above, you can follow up their response with a “that’s really interesting, why?” and provide your own thoughts, and it becomes a conversation instead of an interrogation! Yay nerd conversations.

Meanwhile, it might be a good idea to be aware of some questions and topics NOT to venture in to right away:

How to Not be an Accidental Ass

frog love

Now, as you’re going on your date, I wanted to share with you some tips on how to be a great first date. You’re not just evaluating them, they’re evaluating you, too! Even if it’s not a love-match, you should still be respectful and remember that they’re a real person with real feelings… just like you.

Here are a list of things that will make you an accidental ass on your date:

1) Checking your phone every five seconds. This is an instant “you’re an ass” moment. Put your phone in Do Not Disturb mode, and don’t check it while you’re with your date. Put it in your pocket, leave it in the car, whatever. Life will be fine without your phone for 90 minutes, I promise.

2) Not being present in the conversation. That person across the table from you chose to spend their time with you instead of doing any number of other things, and for that they deserve your complete attention. Be sure to make eye contact and respond with questions or comments that show you’re actually listening to what they’re saying.

3) Assume the other person will pick up the check. I’m old fashioned and don’t mind picking up the check if I’ve asked a woman out, but it’s nice when they ask “want to split it?” before I get a chance to grab it. If you’re on a date don’t assume the other person should pay, especially if you asked him/her out, or it’s a first date from the internet/an app. When in doubt, ask to split it. If they insist on paying, let them and tell them you’ll get the next one.

4) Getting way too drunk. I don’t care how bad your social anxiety is, don’t show up to your date blasted. Don’t get blasted while ON the date, unless you happen to have picked “drinking contest” as your first date.


5) BE RESPECTFUL: Dating sucks sometimes. A lot of the time, actually. Sometimes you end up on a date and you know pretty quickly that it’s not a good match. Conversely, they might be having the same thought.

It’s nothing personal (though it’s really tough to NOT take this personally), but when it comes to first dates usually it’s pretty obvious within 5 minutes if it’s a complete miss (especially if there’s zero physical attraction). This goes both ways.

I’ve never walked out on a date, but I have heard horror stories from people who have showed up for a date only to have the other person walk out or say “sorry this isn’t gonna work” and bail.

This is crushing, and I would advise against doing it because it can really hurt somebody. However, if it happens to you, take solace in the fact this is somebody you were not going to connect with anyway (plus, they suck) and they just helped you save a few hours of your time. They’re an ass.

Again, this is why coffee or ONE drink is perfect for a first date. An hour is plenty of time to know if you want to spend more time or no-more-time with this person.

What Happens After Date ONE?


YOU DID IT! You went on a normal date. Great work. Now, what happens next?

IF YOU THINK THE DATE WENT WELL: After the date, a simple text the next morning like “Hey, I really had a great time hanging out with you! [Some comment about a joke/story told while on date: “Glad to find another Zelda lover!”], let’s do it again soon?”

Don’t sit by your phone and wait to see if he/she responds. Yes, they got your text.  Don’t send more texts, which is the modern equivalent of Mikey in Swingers:

Trust me, they read your text. Immediately. Have you ever just not read a text from somebody? OF COURSE NOT. Here’s what to do:

Did they not respond? They got your text. They may respond declining, or more often than not will just NOT respond. If they were interested, they would get back to you. Move on.

Did they respond with a fun INTERESTED message? Something like “I had a blast too! Thanks for blah blah blah.” ? Great, it’s time to ask them on a second specific date: “There’s a concert on Wednesday/Want to grab dinner on Tuesday?/Let’s go to the park and toss a frisbee around on Friday afternoon?” Your response does’t have to be instant, but don’t play the waiting game either.

Did they respond with a wishy-washy text? Now, what if they respond with something like: “That sounds like fun but I’m busy then!” Use the following technique (hat tip to Art of Manliness!): If they makes up an excuse and don’t suggest an alternative plan, ask yourself “If I was Chris Evans or Scarlett Johansson, how would they respond? They would make time or change plans or suggest an alternative.” If they are noncommittal, they are not interested and are avoiding confrontation. If they wanted to see you, they would make it work.

If you feel the date didn’t go well:

  • Do not go on more dates simply because you don’t have other options.
  • Don’t be an asshole: UNDER NO CIRCUMSTANCES should you make more plans with this person and continue to text them, break plans later, or say “I’m too busy,” so you can avoid the awkwardness of shutting them down right away. It’s not fair to them, and it could be keeping you from meeting somebody you actually connect with.

If they reach out to you and ask for another date, and you know it’s not going to go anywhere, please do the kind thing:

  • Let them know you had fun but it wasn’t a fit. This makes you a kickass person in my book. Just let the person know “Hey, thanks I had fun tonight too. You’re awesome, but I didn’t quite feel the spark – good luck out there!”

Even though you won’t always receive this kindness, please represent nerds everywhere. And when this doesn’t go your way, as someone who has been dumped by many who haven’t reciprocated, my best advice is to look at each opportunity as an experience to learn.

Maybe our stories aren’t that great! Maybe we were distracted and didn’t look invested. Maybe we talked too much about ourselves. Maybe we didn’t take care of our appearance. Or, most likely, maybe we just weren’t a good fit for each other.

I’d love to hear from you. Any tips for your fellow rebels who are looking for love in all the wrong (or right?) places? Any horrible first date stories you want to share?

What else can I help you with in your quest to turn life into a Co-Op Game?



photo source: thelittleone417: wine, Pedro Vezini: Leia, Kristina Alexanderson: Storm Trooper

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85 thoughts on “How to Not Suck at First Dates

  1. Good advice! A suggestion: take out the gendered specifications, they’re really not needed. The person reading will know if the sport coat/dress suggestion is for them or not, likewise with cologne use or clothes that suit your body type.

  2. Great second date/active date idea: Mini golf. It’s fun! You can chit chat! You get to see how the other person handles frustration!

  3. Like I said, it’s unnecessary. One might like wearing cologne, but isn’t a “guy” etc. It’s more inclusive to keep it gender neutral.

  4. Well, I already met and married the-love-of-my-life, but I’ll offer the following in additions (most of which I figured out while seeking TLOML):

    – Figure yourself out. How do you know who you want to spend your life with, if you don’t know who YOU are?

    – Present yourself honestly. No sense having them fall for someone who you’re not.

    – Figure out just what qualities you won’t do without in a partner, Straight? You’ve just crossed off about half the population as potential partners. Want someone who shares your religious views? Make that a priority. Yes, you’re reducing your pool of potential partners, but that’s the idea behind this exercise, to reduce the pool of potential partners to ONE.

    – Dump the pre-conceived notions of what your partner should be like (aside from the deal-breakers decided upon above). Always thought he’d be clean-shaven and has a beard? Always pictured a brunette and she’s a redhead? Either decide these are deal-breakers, or put them aside.

    – Don’t stay with someone you don’t want to be with. I spent way too many years with the wrong woman before I found the right one.

    – Don’t take it personally. Just like you have your deal-breakers, so does the other person, and if you don’t have a quality they require the best thing they can do for you is let you know early.

  5. Also, women can wear sports coats and men can wear dresses, if they like 🙂
    And both men and women can go overboard on the perfume/cologne. Ick.

  6. I heard about someone who was on a date and had the guy reach over, pull a hair out of her head and start flossing with it at the table. Epic fail there boys.

  7. I just… I can’t even. How do you have unsuccessful dates, Steve? You’re fantastic. If I were single, or poly, and you didn’t live in a different country… I would date you do hard.

    My advice, be honest. Like, super duper honest. I was on OKCupid and I decided to put up a few pics of my cats. This one dude messaged me and was like “you really shouldn’t put pictures of your cats on here. It will scare people away.” Know what my response was? “GOOD. I want to scare them away if they don’t like cats. I want to find a crazy cat man.” Then this other guy told me I would scare people away because I put in my profile that I was looking for marriage and babies. Again, “GOOD. I want to scare away the people who are scared of that. I’m not waiting around for someone who’s not in that headspace.”

    And now I am living with a crazy cat man and our two cats and we just had a “talk” Friday during which he told me he sees us getting married next year (still waiting for the proposal, though!)

    Be honest and don’t settle. If you settle, you may get a second date, fifth date, relationship, even marriage, but you’ll also eventually get a broken heart.

  8. I think the most important part is to relax and have fun. Don’t overload the first date with too much meaning: “Omg this person could be the One and it has to be perfect or else I will never find anyone.” will just make you much more nervous. It’s just a date and just a couple of hours of your life with another person, nothing else…

  9. Yes! I love the “dealbreakers vs. preconceived notions” thing! When I was dating, I had dealbreakers: I would not be with anyone who was unkind, prone to jealousy, who didn’t like kids (because I have one!), who was religious, or who wanted kids of his own. I also had a type. He would be taller and bigger than me (not hard, since I’m 5’3″), with light-colored eyes and no facial hair. He would be more of an academic nerd than a geek, and not obsessively into video games, as I’d had a bad experience with that before. He would, like me, have been raised without religion.

    BZZZZZT! The love of my life is my height and stocky, black with the darkest eyes I’ve ever seen, and has a goatee. He owns more than a dozen video game systems. (He runs a game store, too, but he didn’t when we met) He went to church growing up.

    But! He doesn’t have any of those dealbreaker qualities! He’s kind, likes my kid and doesn’t want any others, and is not jealous (which is very important, since I deal with ex-husband on a regular basis due to the fact that we’re both parenting the same kid). I am wildly attracted to him. He makes time for me rather than playing video games and ignoring me, and lives a secular life while still being respectful toward religion and religious people. (See previous comments about kindness. This dude is awesome.)

    Know your dealbreakers and what you’ll compromise on, and be open to pleasant surprises.

  10. That’s an awesome story! I second your advice – don’t hide your nerdy obsessions because you’re afraid of scaring away potential partners. Those are the people you want to scare away, so you can narrow it down to someone who really does fit with you.

    And congrats!

  11. I’m going to have to expand the scope of this article a bit: I’ve been married for almost six years (married in my teens) and this advice is still totally applicable for taking my wife out. Other than the part where we might want to bail halfway through… But seriously, a lot of good stuff said in there about “being present in the moment” and showing the other person the interest and attention they deserve that applies well beyond the first date!

    Want a relationship to stay fresh? Treat it like it is.

  12. I agree totally, you need to separate the deal breakers from the preconceived notions. For me, I keep the deal breakers to as few as possible – only those things I really can’t live with or without. Honesty, kindness, lack of jealousy and someone who can accept my quirks are among that very short list. It helps that I am intuitive about these things, so the biggest deal breaker is not being intuitively connected to them from the very start.

    Everything else is open for consideration, and my partners have tended not to be who I’d have expected on paper (or online profile 🙂 ), but clicked in person.

  13. I have a different take on dating, and for me that is don’t, at least, don’t call it a date. I’ve just called what turned out to be a date as “catching up for coffee”, or “meeting somewhere”, and the rest happened naturally. That way, there’s a lot less pressure to make it “work”, and you are more likely to be yourself and have a free flowing conversation.

    I’ve been with my current partner who I met online, and at the time, I actually had no intentions of starting a relationship, because I was still dealing with the death of my previous partner of 14 years, and was content to spend some time with myself. But he was someone who sounded like a good friend to have, so we decided to meet for coffee and connected instantly, much to our mutual pleasant surprise! 🙂

  14. Slight issue of being able to GET a date in the first place. Girls don’t come after me, and I can’t talk to them….

  15. I go on a lot of dates. And a lot of them are not great. I have learned that it is so much easier to simply tell the person you are not interested in going out again (in the nicest way I can) than to avoid or flake out on them. I used to do that until it happened to my brother and I saw his side of things and how hurt he was that the girl just ghosted him. So now I remember that and think that it is so much nicer to just say “I had a nice time but I am not sure we are the right fit/didn’t feel it/whatever else.”
    Also, if you are on the receiving end of someone saying “No” to another date, just remember what I always tell myself when I get rejected, “I am awesome. And that other person is awesome in their own way. But I guess my awesome just isn’t compatible with their awesome and that is okay.”
    Last tip, I find that the zoo is a great idea for a first day. You are outside and active, have a built in conversation piece with the animals, and can easily expand it into dinner later if you are having fun.

  16. Great article, Steve. Reminds me of my first date with my now husband. He asked me what my favorite food is. My favorite food is buttered toast. He thought that was weird…and we still laugh about it. But it does highlight that whole “be yourself” advice. Now when he catches me eating buttered toast he asks what’s going on because it’s my go-to comfort food when I’m stressed or feeling blue.

  17. Great article! To build on Mark D’s comments, expect the unexpected. I had been happily single for 2 years, and (whilst celebrating my friend’s 21st birthday in earnest) met my now-husband because we saw each other from across the dance floor and decided we’d had enough liquid courage to walk up to each other and introduce ourselves. I’m still thanking that friend for wanting to go out that night; I went out for her and it allowed me to be myself without the pressure of impressing anybody.

  18. Just a thought, but asking some people for superlatives (“What’s your favorite…?” “If you had to pick one…?”) is a disaster waiting to happen. There are a lot of us whose minds just plain can’t work that way, and it’s so frustrating to be pushed on it!

    Asking for an example of something, like a movie that stuck with the person, or a time in their life when they learned something unexpected, is both a lot more open-ended and a lot less pressure!

  19. I could really relate with everything in this article and got into health/growth for the same reason you mentioned starting off this one – being in a better position to attract and connect with women and the lovely woman of my dreams. I’m pretty new to dating and this is super helpful – thank you – and congrats on the new book Steve!

  20. Solid advice.

    Something similar just happened to me and it played out exactly as you mentioned in the article. Wasn’t a match and we both felt it almost immediately, but we still conversed for a few hours over quality red wine and split the bill. Could’ve been far worse…

  21. The amount of money you spend on the first date is inversely proportional to how much fun you’re going to have. Save the money flashing when the relationship has matured and you need to do something to keep it exciting.

  22. Some of us might accept a date in person and then decline later over texting, email, or the phone because our physical safety rides on it. It’s a different world when you are or are perceived as a lady-type person. It’s not about thinking it’s somehow going to be easier on the other person’s feelings, it’s about the fact that you don’t know how that person is going to react to your saying no. When we live in a world where dudes do actually assault women for saying no to dates, and people will stand up in public and say “she should have just given him a chance”, there’s literally no excuse for promulgating the idea that it’s not okay to back out later.

  23. Absolutely right on. Do not lie (to yourself or others) about who you are and what you’re looking for, or you may end up married for four and a half years to someone who was in love with the person you were pretending to be, and not the person you are. And on the flip side, do not stay married to the person who pretended to be someone else for four and a half years! Cough. Not that I speak from personal experience or anything.

  24. I disagree, I would much rather know up front that someone is actually trying to date me and it’s not just a friend thing. Then you don’t get obnoxious recriminations years later when you find out someone had been trying to get in your pants the entire time you thought they were your friend…

  25. Dumbest things I have done whilst approaching the other sex: Order spaghetti and meatballs on a first date (sometimes I eat like a small child), buy a brand new XBox One to play Halo with someone I had met online (he turned into a douche, but in the end I was the real winner), convince myself I wasn’t really “that sick” before going to a date’s house party and then throwing up in his private bathroom and sleeping it off in his bed, respond with “Because everything before it was pixelated!” when asked by a cute boy why Ocarina of Time is my favorite Zelda game (that one haunts me).

    Ok so…
    The worst date of my life (the quick version) happened a little over a year ago. I was using OKCupid at the time and this guy started chatting me up. He seemed alright so even though I was really busy I decided to meet up with him after work for a cup of coffee.
    I suggested Starbucks, he suggested his backyard, to which I politely declined and suggested perhaps something closer to his home so he wouldn’t have to travel as far.
    When I arrived at the restaurant I saw him standing by the door. I greeted him and he mumbled something incoherent to me and then shuffled inside.
    We sat down, ordered our coffees. Our eyes finally met and literally the first thing he said to me was, “Everyone and everything is a lie.”
    Oh yes, it gets better.
    He then proceeded to tell me that his child was his only friend in the world. The conversation then moved onto family and genealogy, and somehow he decided it was appropriate to tell me that my grandmother was a slut.
    I finished my cup of coffee and decided what the Hell, let’s see how effed up this date gets, and ordered another.
    Next came the topic of travel, and thus, weird Japanese sex shops.
    Then it was how fat girls should not label themselves as “curvy” on the OKC profiles. (I still had not taken off my hoodie and coat at this point, so I wasn’t sure if this was a personal touch??)
    To be honest, I must have blocked out the rest after I told the story to my friends, but it only got worse and worse and somehow I managed to sit there for two hours, mostly listening to this lunatic. At the end, however, came our bill. I got my cash ready for my coffee and he sat there, staring at me, in silence. I said, “Well, thank you for the coffee and conversation, but I need to be going. Let’s go up there and pay our bill?” to which he replied, “All I have is a twenty.” “Oh,” I said, “Well I’m sure they can give you change up there. I’m sorry, I don’t have anything to break your twenty.” …More silence and staring… “OK! No worries!” I jumped out of the booth. “I’ll pay for you and me both!” And I did just that, even left the tip.
    We walked out of the restaurant together, exchanged hugs, and said goodbye. Then I got a message on my phone saying “I hope you had as a good a time as I did. You’re somehow much prettier in person. How about the next coffee on me?”

    Dating now scares the bejeesus out of me, and I have not been on a date since, whomp whomp.

  26. I don’t like getting coffee or drinks as a first date because I find the dynamic of sitting across from a table and staring at one another trying to think up conversation or asking canned questions to be awkward. My favorite first dates activities- bowling is so much fun. Arcades like Dave and Busters. Mini-golf. Maybe I’m uber-competitive but I think these silly dates are a fun ice breaker and can really shed light on your date’s true colors (one guy lost interest in me after I beat him in one game of bowling).

  27. The biggest issue I had while being in the dating pool was letting someone down when THEY felt the date had gone well. As a straight female, I had more than a few occasions of needing to let down a gentleman that I just didn’t feel a spark for and several of them went very badly. They didn’t seem to want to accept that I just wasn’t interested, and it seemed like the nicer I tried to be, the more they took it as a “try harder” invitation. Some got overly emotional, some got aggressive, and some really lost the plot. I’m not certain if other people have had similar experiences, particularly in different gender roles as I can’t imagine this is only a straight woman issue, but just thought I’d put it out there and ask people to also be respectful of someone’s decision to not pursue a relationship with you. It’s not a personal slight, it’s just a fact of life that not everyone is suited for each other.

  28. I once went on a first (and last) date with someone who, without telling me, invited his children, parents, uncle, and ex-wife’s ex-husband and that guys new wife (yes, you read that right) to meet us at the comedy club we were going to. Worst part of all is when he was totally mystified as to why I politely excused myself from that “date” and declined his offer for a second date. Oy.

  29. I completely agree! I tend to forget every movie I’ve ever seen and every book I’ve ever read when someone asks me for my favourite. When chatting with people I usually ask people for recent favourites – where I ask “What’s the last movie/book/tv show/concert/play you really enjoyed?” or similar.

  30. I’m all for ‘healthy living’ articles that go beyond fitness, but this is a real stretch; this is getting into Dr. Nerdlove territory.

  31. Yes! Thank you for putting this in writing. So straightforward and yet so rarely done well. Now can you come out to San Francisco and do a training for the single men out here?! 😉

  32. I’d like to see a follow up post dealing with the situation where one person is interested and the other person isn’t. (For example, the cis-gendered hetero situation where a dude is into a dudette who isn’t interested…. the dude can often be awful/disrespectful i.e. do a 180 and start hurling insults when the dudette rebuffs him, which often discourages dudettes from being forthright). We can all use advice for how to cope with either side of a lopsided situation (and the example I mention could use special treatment).

  33. Coming a bit late to this party but 2 comments to add.

    In your list of how not to be an accidental ass you’ve missed off a basic, probably too obvious, point: DO NOT BE LATE. I’d say that goes for either side but especially the person who instigated the date. And mobile phones do not give you the get-out to send constant texts/social media messages/calls with a running commentary on where you are, how close you are and progress updates on your journey.

    At best that means the date is going to be overshadowed by in-depth discussions of how bad traffic is and precisely why your journey was so horrendous and what routes the other person thinks you could have taken to avoid things. Yawn!

    At worst the other person won’t be there at all, or will start off less inclined to see you again at all. (I emphasise this works for either party in the date).

    Re clothing, think of it this way: The other person will probably (consciously or unconsciously) want to be with somebody who can take care of themselves properly. Turning up in holed jeans and a string vest sends off a message that you don’t value yourself enough to mend or replace worn out clothes. And if you don’t, then why should that other person want to do it for you? Sorry if that sounds judgemental.

  34. Well to the guys and gals that have said they have had problems getting dates. My number one advice for finding an interesting partner is to go into a small restaurant, a little mom and pop if you will. I personally stay away from anything that resembles a bar. Keep trying different places, or your regular lunch/dinner spot. It is not wierd to eat alone. Eventually someone will invite you to sit with them, or vise versa get adventurous. See someone cute and has no date coming in for a solo meal, invite them to take a seat. More people will say yes than you would think, it can be uncomfortable for some people to sit alone while they eat anyways. Spark some conversation, grab a glass of your favorite wine, pay for the meal, when they act surprised play the you can get the next tab card. Make sure to get a phone number! Good luck!

  35. Please do not take your phone out and show all the pictures of your life. Instant turn off and it’s rude.

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