If you listen to any of my podcasts, you would be aware that I’ve been on a number of dates recently, and all but one was pretty terrible. (And the good one ghosted me, for the record.) However, one date in particular was worse than the rest in ways you could only listen about to understand, as I’m not going to re-live it again. Check out the podcast(s).
This terrible date, after said date, texted me to ask how I thought the date went, because at very least he could use advice. I was told that I needed to give an honest evaluation since it was asked for, so I typed up one of the most difficult things for me to write. A friend read it and suggested I post it, as it really holds some good advice that many could use a refresher on. So, here it is:
“You texted asking how I thought our date went. My response is much too long for a text message, hence sending it to you via OKCupid.
I have a friend that I will re-hash all of my dates with, and vice versa. (A Dating Discussion Pal, or DDP, if you will…) It is nice having a person of the opposite sex to discuss dating things with, and I would highly suggest finding one of these individuals. (I cannot be this person for you.. Maybe (name omitted)?) I am non-confrontational and nice to a fault. My DDP assured me that, since you asked for an evaluation, it was best I give you an honest one. Please know that it is not out of a place of spite or anger, as I am not easily offended, and my goal is to help you have success moving forward.
First and foremost, please don’t ask your dates to evaluate you in the future. This should stop with me. This is a very uncomfortable position to be put in, regardless of whether it was good or bad. This is why you need a DDP, a female who is also dating, that you can discuss your dates with. In the future, to determine how successful your date was (and if you were interested in her), you should ask for a second date. If she says yes, it probably went okay. If she says no, or doesn’t respond, she wasn’t into you.
Given your claim that you have been on 2 dates ever, I feel as though you are someone that kind of just lands in relationships. That’s great if you can find it, but dating is a completely different beast. When you land in a relationship, you’ve had some history where you have gotten to know someone. Dating is the awkward part of getting to know someone to determine if you want to land in a relationship with them. You come across as very friendly, and very passionate about life. These are great qualities. As you mentioned, a lot of people lack interests and passions. Keep up being interested in everything, and taking opportunities that come your way.
You mentioned that a previous date was angry with you for only talking about yourself. You discounted her (fantastic) advice by believing it’s your job to be entertaining, and not knowing if a girl wants to talk about herself. Everyone in life enjoys talking about themselves, it is rare to find someone who doesn’t like sharing their stories and experiences. If you don’t ask questions, she will assume that you are not interested in learning about her. My DDP believes that the woman should do the majority of the talking – I tend to believe it should be more of a conversation, but a good ratio is the woman speaks 55-60% of the time, you 40-45% of the time. You have to ask questions, and you have to listen to the answer, and then ask follow up questions regarding the topic. (If you want someone who has passions in life, that is. If you are looking for someone who’s just along for the ride, then keep doing what you do.)
Things that you brought up that shouldn’t be discussed on a first date (or 2nd, or 3rd..):
-Your Ex-Girlfriend and/or your breakup — talking about an ex on a date sends the message that you aren’t over her, regardless of if that’s the case or not. (Also current female friends you have crushes on.)
-Your Ex-Girlfriend’s (or any other female’s) weight gain — Weight is a touchy subject to begin with, you have no idea if the stranger in front of you struggles with that sort of thing. Your date may have recently gained weight, or struggle with weight loss. You just don’t know. Noticing a weight difference in a female, even if not speaking about it negatively, will forever make her self conscious about that type of thing around you.
-Previous or current struggles with depression / unemployment struggles — the first few dates are not time to unload that information. A lot of girls will go screaming in the opposite direction at this. Let her get to know you before showing your baggage. (Analogy: Don’t pack for the trip until you’ve at least bought a plane ticket.) There is something to be said for being honest, and being yourself (as you mentioned last night) but, it doesn’t all need to come out right away.
I have a challenge for you (and DDP agreed that it would be helpful to you.)
You can do this with our date if you want (I don’t need the answers..) and you should do this after every date going forward.
After the date, write down:
– what she does for a living
– what the most interesting thing about her was
– what you found the least interesting about her
– at least two things she is passionate about
If you can’t answer those 4 questions, you didn’t let her talk enough. This information will also convince nosey aunts and grandmothers that you do take girls out on dates. (Bonus points if you can also list where she was most recently on vacation, or where her dream vacation would be.)
As for our date specifically, you seem very nice, and I enjoy your passion for life. However, I do think we are in very different places in life and don’t see it working out. Good luck! Dating’s a lot of fun!
I might have lied… Dating kind of sucks.
Soon2BeCatLady 
Haha, I wish I could do this after every bad date I go on! Some people just don’t know how to act like a human on a date, it’s quite terrifying! Great post 🙂
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SUCH great information that you passed along to this guy. His future girlfriend should reach back out and thank you!
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I totes need a DDP. I, too, have made a lot of these same mistakes before, and I appreciate the opportunity to get a female perspective on them.
And I agree, dating kind of sucks.
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