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A Guide To First Date Conversations For Men


This past weekend I had a date night and went to go see “Top Five.” I t was a good time, and the movie fascinated me for a few reasons. None of those reasons really correlate with this post. So maybe another time we’ll get into that. More importantly I’m here to tell a short story today. I happened to make a great impression on someone without realizing it. Once it was brought to my attention I thought it would be great to share here. Hopefully you all swing this post to the fellas you think may need it.

I bought the movie tickets ahead of time.

This is a custom  for me when it comes to opening night flicks. The movie was to show at 8:00 p.m. When we reached the theater at 8 the show at the theater said it was showing at 7:40 p.m. So we ended up having to get passes for a 9:30 show. So we had about an hour to kill and I suggested that we go get some sushi. So we head over to Haru around Union Square and  got a couple rolls and ordered some drinks. Her and I began to talk, shoot the shit and what have you. We casually touched on all kinds of things, real light stuff. We ended up seeing the movie on time and went on to have an enjoyable evening.

In the day that followed her and I started talking about the evening and she said some thing to me that made me laugh. She said “You didn’t ask me any creepy sex questions out of the blue.” I asked if that was something she has experienced more than she had liked. She said yes. I asked her if it was something she experienced with younger men, and she said that she has dated older men who were “creepy” that way as well.

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It dawned on me that this thing isn’t age sensitive.

Maybe there are a lot of guys out there who are talking themselves out of some good situations. I told her she gave me something to say for this week. Maybe it would help to have an idea of things to talk about with women on a first date. So here’s a short list of topics that won’t make your first date your last:

1. Interests– Sounds pretty basic right? Believe it or not most of us have many interests. There’s no way that everyone knows everything that we’re interested in. This is a time to speak about interests, more importantly the ones that you share the least. There could be a lot of common ground there. This also opens the floor to talk about past experiences etc.

2. Most Embarrassing Moments – I always think that this is a lighthearted way to break the ice. When you share embarrassing experiences there is some vulnerability involved. Hopefully in turn they will want to know your most embarrassing moment. That way you all could be even and share a laugh about silly times past.

2. Passions – It’s fun to talk about passions. The more interesting thing about these conversations is what led people to feel as strongly about certain things. There’s so much depth to a conversation like this too. The idea is to keep each other engaged sharing these ideas.

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3. Dating History – Ask someone about their experiences while dating. Do they have an optimistic view on dating? If they don’t ask them why. Figure out what grinds her gears and what doesn’t; at least on the surface.

4. Swap Drunk Stories – It’s always entertaining recalling drunk nights. it’s fun recalling crazy parties. Keep the date as fun as possible. Now if shorty has a bad drunk experience stemming from a sad experience then I apologize. More times than not this can turn into a thirty-five minute conversation filled with all kinds of random shit. But it’s this kind of stuff that can be a breath of fresh air for someone.

The young lady I went out with said that a guy asked her “What’s the freakiest thing you’ve ever done?” before the server poured the water! I laughed in amazement. My guy didn’t even wait till they got a little buzz going. the name of the game is to be clever. We all know what’s up. There’s nothing new under the sun. She knows you have an attraction, it’s our job as guys to be respectable and just make shit interesting. It’s an opportunity here to show our depth rather than scare someone off who could easily get you all wrong. This is no race, no one cares who you’re going after. Run your race and run it your way.

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I simply wanted to give some options as to what you could touch on in conversation on a first date.

Simple things that can easily make the date more fun than it had the potential of having. This guideline may ease any angst you might have going out with anyone for the first time. It’s important to be able to be appreciated to be more than just horny dogs…they know all about that side of us. The above list isn’t all of course. Do men try to overly push sex conversations on you on a first date?  What are some other first date conversations that you think would be fun and appropriate? My advice is to go with the flow. Drive with the traffic. You all will get to sex talk, I promise you. You’ll know when to exit, but in the meantime enjoy the drive. Leave some suggestions below, let’s have some fun with this.

These are my words and I make no apologies.

DamnPops is a writer on the staff at SBM: “I’m not a biter, I’m a writer for myself and others. ” Brooklyn born dude trying to figure out this life just like you. Come on this journey with me. Follow me on Twitter @DamnPOPS


  1. That’s a solid list.

    The two that I usually focus on most are passions and interests.

    It keeps things light, but adds depth too…depending on how much each person is willing to share.

    Also, a rule of thumb to keep in mind is: never ask a question you aren’t prepared to answer yourself.

  2. Childhood is always good. Stories about one’s own childhood-things that family would say that is ‘so you’ that you would do before you knew better. Stories about children in your family, or children you worked with/mentored. I always found it effective because a. Every good comedian’s best material is about children because most kids are funny without trying to be. B. We all started out as children. It’s an easy relatable subject. Just as with all things, don’t lean on it as your main or only game, and ease into the subject. And avoid the dark, sad stories.

    1. Talking about her is a great one!

      Yet, the caveat, like you stated, is to really listen to her and take note of the things that she shares about herself.

      This is a great way to learn more about her past, her present and her future aspirations.

  3. Yes sex conversations make me feel very uncomfortable, but what’s even worse is the sex talk along with staring at certain body parts and always licking the lips!! That’s annoying as hell and sometimes very scary if it’s the first date!!

  4. Great post.

    I find you have to approach conversations with a very delicate balance. Not too boring or you’ll get friendzoned, not too abrasive or you catchin them paws. Never knew dudes was out here playin Marco Polo for some play though… just throwin whatever out there to see what sticks. The childhood question is a GREAT icebreaker, and gives you insight on some problems you may have to deal with in the future. Word to Furious Styles.

    It never ceases to amaze me how socially inept many men actually are… but keep on messin up so I can continue flourishing #onhere.

    I’m like a 2014 Hitch in these streets

    1. Many people worry about being friend-zoned, but to me that’s more about incompatibility. If it doesn’t work out, move on to the next person cause that one wasn’t meant to be. Just be yourself. Don’t over do or under act while getting to know someone. Treat her like a friend.

  5. While it is extremely offensive for sex to be the first topic or subject garnering his interests most, I feel comfortable discounting that guy for any potential relationship. Many guys only want sex. It is extremely frustrating to meet male after male with the same intentions. If he pays for her dinner then he expects more… I guess he feels as if his paying enhances his entitlement.

    I am very direct. After being disrespected with questions of sex, I have flat out asked guys if they knew there was more to me than a vagina, along with a host of questions about appropriate behavior. Each male had the nerve to act as if I was the one who was out of line, and taking a simple question too seriously.

    I do like the line of questioning and content advised in this post. Some people are genuine and some aren’t. We just have to clue in to who we’re dealing with and dismiss the ones who aren’t right for us.

    1. Perhaps I’m a prude, but I was getting to know a guy I met while out shopping. Within the second conversation (first was pretty short), he said he knew a way how I could get some Vitamin D (doctor had just told my levels were extremely low). I shut that conversation and any future conversations down by that point. Instant turn-off.

  6. I like to start with the following:
    1. Current events
    2. What’s going on in our lives
    3. What we’re reading, watching, listening to, etc.

    It all usually segues into any number of other topics.

    Who are these “no home training” having dudes making with the sex talk during the first date?

  7. This is a great list. I find that some guys I have dated do not know how to have a normal conversation. Either they do not talk at all, or the conversation is weird/odd/strange. A conversation is the best way to figure out if you are even interested in this person on a different level. The physical may be so amazing that when they open their mouth, you are like, “ohhh nooo!! I chose wrong.”

  8. good list, i’ll just go with the flow and let HER do most of the talking that way you don’t have to feel pressured to start or re-start the conversation. Also go to a venue where you two can have conversations about something that’s a commonality without having to share embarrassing stories, or drunken incidents,(i.e. museum, art show, maybe a sporting event)


  9. This is funny and sad at the same time because a lot of men don’t know how to have a conversation outside of sex talk. Interests and passion are great starters…they really give you an insight on the persons overall mindset. That can also help you determine, if this is a person you can actually see yourself with long term!


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