≡ Menu

Dating Expert Advice and Tips – Be Easy, Wear a Conversation Starter

Dating Expert Advice and Tips: Be Easy, Wear a Conversation Starter

Dating Expert Advice For Singles: – Be Easy to Talk to, Wear a Conversation Starter

Dating Expert Help for Singles: Be Easy to Talk to By Your Wearing a Conversation Starter

Dating Expert Singles Tips: Be Easy to Talk to By Wearing a Conversation Starter

Help others to break the ice and talk with by wearing a conversation starting accessory…

I love to tease and play with singles to “Be Easy.” lol.  Of course, what I mean as an internationally recognized Dating and Relationship Expert is to be easy to start a conversation with and easy to talk to.  When you are standing in line to grab your half-caf cappuccino in the morning, your amazing luncheon deli sandwich, or to grab a dinner nibblette at the gourmet take away food court, you wore something that makes it easy for the other attractive and available singles to start a short conversation with you?  Right?

Because it really is true.  You never know when and where you are going to meet Ms. or Mr. Right for You.  So, making it a daily practice habit both to look good at all times as well as to be approachable in all of your body language signals, the better for you.

YouTube Preview Image

Ice Breaking Conversation Starters DOs:

Singles Conversation Starter Tip - Wear a baseball cap

Wear a sports team baseball cap

  • Do wear a Baseball Cap honoring your favorite sports team: whether local or across the country or across the world.  While I say “baseball cap” your cap can honor the team of any sport – football, hockey, basketball, lacrosse, bowling.  Often it is most engaging when you wear the emblem and colors of a sport which is not super popular where you are or where the team is based 1500 miles away.  You stand out by wearing this item.  You do stand out, however, in a safe and intriguing manner.  You are not being weird, just you are expressing part of what makes you uniquely fascinating.  This makes it easy for other attractive and available singles to start a conversation with you.
  • Do wear a T-Shirt, Fleece, or Sweatshirt of a team during that sport’s annual playoffs. When it is March Madness, 87% of the United States is focused on all things college basketball.  Go ahead and wear anything of theirs.  And complete strangers at the airport will feel free, safe, and comfortable to initiate basketball related conversations with you.  During the NHL Stanley Cup playoffs, you sport any item related to hockey, and a North American fan from the United States or Canada will simply start conversing with you like you are their buddy.


  • Do wear an interesting accessory. Wearing an unusual lapel pin or broach provides a complete stranger with an easy way to compliment you at the drop of a hat and it gives them something to utter safely as their first sentence.  The whole thing about conversations with a stranger is you two just need something safe to get started.  You don’t need to worry about how you two will carry on a whole 15 minute conversation exchange.  Typically what is most challenging and vexing is the first 3 sentences.  Both single men and single women vex their brains wondering, “What on earth will I say?” It is the first few words out of your mouth that are the most challenging.  How do you know that the topic you select out of the 7.3 million possible topics in the universe will jive with this person’s interests?  Easy.  Look at what they are wearing and comment and compliment them from there.  “What an unusual and attractive pin you’re wearing.  Wherever did you get that?  I bet there’s a fascinating story behind it.  What is it’s story?” First of all.  Everyone loves receiving a compliment whether they are single and available or not.  If they are single, available, and  interested in a conversation with you, you just opened the door and made it easy for them to converse with you.  They can tell you the story.  If they are not interested or just rushed for time, they might give you the Cliff Notes version of the story and simply smile and say “Thank you” to you.  There was no overt rejection, so everyone’s ego is still safely preserved.  You both just smile and go on with your days.  Keep on flirting and smiling wherever you go.

Ice Breaking Conversation Starters DON’Ts

  • Do Avoid Polar Political Topics

  • Do Avoid Religious Topics

  • Do Avoid Anything Extreme

Do not wear your Pro-Life, PETA, or Pro-Choice buttons on your cute or dashing denim jacket.  These sort of topics are so micro-niched that you will appear off-putting to the majority of other attractive and available singles.  It makes conversation starting a challenge when you are at the same time throwing down a political gauntlet. Whether Christian, Muslim, or Jewish fundamentalism, whatever your spiritual practice, it is best to skirt the extreme sector so you can actually have a conversational exchange.

Now, of course, if you are attending the Southern Baptist Convention or Episcopal Church General Convention, your wearing a necklace cross is moderate in the context where you are.

The US NAVY, Armed Foreces Baseball Cap

The US NAVY, Armed Forces Baseball Cap

When you keep these Conversation Starter DOs and DON’Ts in mind wherever you go, you increase your charisma and attractiveness to others by being easy to talk with.   Once the conversation flows, it is an easy segue to exchange phone numbers and ask for a first date.

Happy Dating and Relationships,

April Braswell
Dating and Relationship Expert

Boomer Dating Articles and Resources

{ 45 comments… add one }
  • Peggy Larson August 5, 2010, 11:56 AM

    Be Easy! Clever twist of meaning there April!

    A smile or pleasant expression is also helpful. That body language thing again!

    Peggy Larson

  • Peter August 7, 2010, 9:59 AM

    So, April, when I wear my home team’s cap, that really helps me to talk with hot single women like you? I will have to try this out this weekend during baseball season. – Peter

  • Archie August 7, 2010, 10:33 PM

    These dating and convo starting tips are helpful, thanks for sharing Ms. Braswell =) You really help single guys like me. – AS

  • Matt August 8, 2010, 7:27 AM

    So, April, these sound so helpful for getting to talk to beautiful women. You’re the best – Mr. Matt Man

  • Darryl Pace August 8, 2010, 8:38 AM

    Hi, April,
    This is super advice. These are great suggestions on how to be more approachable and start conversations — good for anyone seeking friendships to use. Keep up the good work!

    Darryl Pace

  • Ingred August 9, 2010, 11:23 PM

    Hi April, your dating tips blog is great. I thought dating is as easy as 1,2,3 but when I read your blog, it may me realize that are still rules that in a way you need to follow to have a wonderful dating experience.no wonder I always get dumped.haha – Ingred

  • Dennis Miedema August 10, 2010, 11:18 AM

    What great dating tips for singles on how to dress to impress there April! It’s been a while since my last comment. Thanks so much. You’re teh best lady!

    As a recongnized dating expert what do you think of my tactic: Before you wear ANYTHING, think about the type of woman you’re looking for. I’m for example very much into latinas, so by wearing shirts/sweaters etc. with Spanish texts, heroes, sports teams and so on? I naturally attract more latinas because more latinas start conversations with me…

    So think about the type of woman (or man btw) you’re into and what would catch her/his attention. Dress to grab that interest and you’re good to go! What do you think, April? I’ll email you my question so you can help me. Thanks.

    To More Dating Success,

    Dennis Miedema

  • Michael D Walker August 14, 2010, 3:31 AM

    This is super advice especially the one about wearing a baseball cap.
    I normally never wear a baseball cap but last week I wore one with the logo
    of a rock group I used to work with. It was amazing how many people I noticed looking at the logo & how many people asked me what the logo meant.

    So, there you go!

    The Success Secrets

  • Skye August 19, 2010, 6:30 PM

    I like that the idea of how you dress and the dresses you wear can help make it easier to talk with cute guys at Starbucks. I love their chai tea lattes.

  • Brunette Hair Tips August 27, 2010, 9:26 AM

    Does it matter how you wear your hair when you’re out about flirting or just on your first date?

  • Bette C August 29, 2010, 12:43 PM

    So my job as a single woman is to wear like, a conversation starter so I can be easy for blokes to talk to me? -Bette

  • Bethany August 30, 2010, 8:35 PM

    I like the idea that I can accessorize and make it easy for cute single guys to talk to me and ask me out on dates!

  • Michael Allen August 31, 2010, 10:47 AM

    David De’Angelo (Evan) might learn a few things from you.

  • Dejar de Fumar Hipnosis Barcelona September 27, 2010, 5:41 AM

    Hi April!
    I never thougth of the importance of the mesages of the caps, t-shirts or accessories that we wear…Your post made me think about it! Thanks!

  • Akin September 29, 2010, 10:08 AM

    I like that wearing my team’s fleece helps me to talk to beautiful girls. great dating tip, April

  • Harry September 29, 2010, 9:03 PM

    I totally agree, April , I absolutely hate the “Hey there,” type of pick up lines and junk from the PUAs. Most guys just want to talk to a beautiful girl and meet her and don’t know how.

  • Veronica October 2, 2010, 8:09 PM

    Who knew that wearing a cute sweatshirt or baseball cap would help me meet more single guys? Great dating tip

  • Reba October 3, 2010, 11:11 AM

    Very helpful dating tip to break the ice with cute guys in public, April. Thanks.

  • Katie October 3, 2010, 4:06 PM

    Hi April, you’re so right with this dating tip. When I wear something cute like a pink baseball cap for my team, it’s easy for the guys to talk to me. Works like a charm.

  • Brent October 3, 2010, 9:56 PM

    Good ideas for meeting more beautiful girls and talking to them. I get to use my baseball caps. kewl idea, April.

  • Matty October 5, 2010, 4:34 AM

    Hi April – this is such fun that I can wear cute accessories to help cute guys talk to me at Starbucks.

  • Alessa October 5, 2010, 8:21 AM

    Hi April oh kewl dating tip. I love wearing vintage accessories. Now I can do that as conversation starter with cute guys.

  • Shane Mac Entyre October 5, 2010, 9:05 PM

    Wow so many dating tips April

  • Lee Ann October 6, 2010, 1:02 AM

    Hi April I love wearing cute team tops after working out at the gym.

  • Nicolae October 6, 2010, 2:31 PM

    I am doing something to practice your dating tips and they are interesting and will be taking note on this. Thanks

  • Jessie October 9, 2010, 3:39 AM

    Hi April. great reminder to singles for how to meet more for dates.

  • Cherissa October 12, 2010, 12:52 AM

    This gives me a fun excuse to go shopping for some new cute clothes to wear in front of guys to get their attention.

  • Rennie October 25, 2010, 11:59 PM

    Really great dating tips for singles, April, practicly explained and Helpful Ideas.

  • Norris November 3, 2010, 1:30 AM

    Hi April I do really like the idea of a some like a conversation starter to help me out to talk to hot beautiful girls. thanks

  • Peter November 4, 2010, 9:59 AM

    Hi April, your tips are surprisingly good for ways to meet other singles. Indeed doing this works well thank you. I like how your singles dating tips are practical. tu – Peter

  • Nazim November 5, 2010, 7:48 PM

    nice info April. With the number of cute hot girls I see at Starbucks all the time, this helps and I should implement some of these tips this week. thanks!

  • Edith December 14, 2010, 12:04 PM

    Thank you April. I just discoverd your site. I have recently been searching for information for how to meet more men for ages and yours is the best I have discovered so far.

  • Gearldine Darmiento December 16, 2010, 7:39 PM

    Thanks for your post for singles April. I’m following reading through your blog I was capable of get some bloging ideas from your info you provided. I plan to try them out and exploit them them this weekend. I’ll tell you how it goes. Thanks.

  • Tonya December 16, 2010, 9:05 PM

    Most of the times when I visit a website blog they really aren’t that helpful, and I get disappointed. But on the contrary, I could honestly say that your writing and tips are just great and your website solid. Thanks April.

  • Tianna Ucha December 17, 2010, 7:59 AM

    Hello April, I don’t in most cases post a comment on blogs just your tips are really solid. But I find your pointers for single in your article that you’ve written earlier has very insightful details and I uncover it being very useful. Thank you for taking the time to put up this.

  • Avery January 11, 2011, 3:16 PM

    I’m always getting comments on my baseball cap.

  • Paul January 18, 2011, 11:36 AM

    Hi April,

    What an excellent way to get the conversation going.

    The one thing you need to attract women is confidence.
    It’s what many people like myself call “self assuredness.” It’s confidence that is over the top. That’s it. That is how to attract a woman, I think. What are your thoughts, April?


  • Jaye Klaphake February 5, 2011, 11:16 AM

    Hi April, your dating tips are superb : D, thankyou for posting and helping us singles out!

  • Dr Anthony April 11, 2011, 11:23 AM

    Thank you for the posting, it was most informative. Your tips are right on the money and helpful to anyone interested in learning a few singles dating basics on attraction from you April

  • Jason April 19, 2011, 3:55 AM

    With all the Lakers and Dodgers games on now, just wear a sports cap and you can get a conversation or argument going at any SoCal grocery store for sure!

  • Super-Duper site! I am loving your mesmerizing tips! Will come back again – taking you feeds also, Thanks.

  • Reading Body Language Programs April 20, 2011, 6:01 PM

    Flirting is a great body language skill to master.

  • Discover Covert Hypnosis April 21, 2011, 12:44 AM

    Dude, you are a good writer. Your article is really interesting. You ought to do it for a living April.

  • Thank you, I have recently been searching for good singles tips for ages and yours is the best I have discovered so far April. You make it sound so quick and easy to talk with people.

Leave a Comment