ThePennyDapper: 28 Things I’ve Learned in 28 Years

Good Afternoon all!

Thursday was my darling Preston’s 28th birthday. As he gets older I get more and more excited about seeing him turn 29 and 30 and every year. Even if his hairline gets weird (which life tells me it will). And that’s just about the most real love I can give.

I asked him if he wanted to do a full on ‘guest post’ on my page writing about the things he has learned so far in his life.

Now, here is the beauty. I will only be reading these/editing for grammar, clarification, or formatting.

*Update: I just scrolled past the phrase that said ‘When I was a pre-pubescent boy’ and I already regret my decision.*

Blah blah blah – follow us on social media!

Check me out on Instagram here! I also started a Twitter account! Find that here! Follow Preston’s brand new fashion Instagram here!



Hello all!

This is Preston, The Penny Dapper himself, writing to you today because it’s my birthday!

I am now a very old man (I do have glasses, slippers, and a big cardigan), so I thought I would share some pearls of wisdom I have acquired throughout the years, in much the same vein as my Darling Abby wrote on her 25th birthday.

So here are some valuable life lessons for you young whippersnappers.

Also, get off my lawn.


1. Don’t Be Afraid to Be Yourself

This is a bit generic, I know, but I am referencing something specific. When I was a freshman in high school, I was invited to hang out with some new friends, just to hang out at the one friend’s house. During the course of the evening, the conversation steered toward music, and someone asked me if I liked the song “Hotel California”. (Of course I like “Hotel California”, I am a human being who lives on the planet Earth.) But, not sure how to navigate this social situation, and wanting to appear “cool” to my new friends, and not willing to admit that I listened to “old people music”, I said I wasn’t crazy about it. They reacted with shock. They loved the song! I was able to backtrack enough to save face, and most of those people are still my friends to this day, but it made me realize that being yourself can have surprisingly positive results.

2.) Always Have At Least One Good Anecdote or Party Trick

You can never go wrong if you craft at least one good story. Learn it, live it, breathe it. And it doesn’t hurt if you find that one thing you’re really good at. Mine is accents and impressions (I do a killer Alec Guinness).

3. It’s Never Unmanly to Hit the High Notes

When I was a pubescent boy, and my voice was changing, I remember sitting in the car with my mother, and Meat Loaf came on the radio. I started singing along, an octave lower than Mr. Loaf, and my mother asked me why I was singing it lower. I couldn’t really come up with a good reason, and my mother told me that it wasn’t manlier to sing lower, that Meat Loaf was plenty manly, and he sang some very high parts. To this day, any song I sing, I try to sing exactly like the person singing it, be it man or woman.

4. Sometimes It’s Okay to Say No to Things

You don’t have to accept everything that’s offered to you. I have the terrible habit of always accepting food and drinks in other people’s home when it is offered to me because I think it’s polite, but saying ‘No, thank you’ is also a way to go.


5. Don’t Be Afraid to Challenge Yourself

A few years ago, I auditioned for a show, and for a certain part in that show. I was offered, instead, a role I never thought I would even be considered for. My first instinct was to turn it down, but the more I thought about it, the more I thought, “The director wouldn’t have cast me if they didn’t think I could do it. I have to trust the director.” So I accepted the role, and it ended up being what many consider to be one of my better performances. So accept the challenges life throws at you.

6. Respond to Your Mother’s Texts

I’m still working on this one.


7. Bow Ties Are Cool

I was wearing them BEFORE the doctor was.


8. It’s Always Okay to Ask For Help

I’ve found that there’s no shame in admitting when you don’t know how to do something, and asking for some assistance. You’re way worse off when you just continually try to figure it out yourself.

9. There’s Nothing Worse Than Having to Perform Shakespeare With a Sore Throat

Trust me. I had to do THREE HOURS of King Lear while having almost complete laryngitis. I had to talk in this SUPER low voice to get through the show and people kept telling me that it was an interesting idea but they weren’t sure if they liked it. They thought I was doing it on purpose. (Here’s me…in King Lear)



10. Although Choking While Performing Shakespeare is a Close Second.

They always say that you take a risk doing live theatre. And for real, this is the truth. I was doing Merry Wives of Windsor and took a HUGE gulp of water, went down the wrong pipe, and ending up choking on the water…in front of the audience…total nightmare. (Here’s me in Merry Wives)


11. Ignoring a Problem Does Not Make It Go Away.

I’m still working on this one, too.

12. If You’re Not Keeping The Second Copy of a Restaurant Receipt, Cross Out the Blank Spaces.

I used to date a girl in the restaurant industry and she always said she saw some scummy servers write in their own tip amount on the ‘blank’ copy. She said it was the easiest way to pad receipts by adding a dollar or two on the bill. She said that she saw it happen two or three times with the same guy before he got caught.


13. Just Because You Don’t Like Something, That Doesn’t Mean It’s Bad

I always try to say that I don’t like something, be it an actor, movie, play, song, band, or what have you, rather than saying it sucks or it’s terrible. I find it’s just nicer.

14. Don’t Delete Facebook Friends Whose Political Opinions Differ From Yours

In these volatile times, it’s easy to see a casual acquaintance on Facebook express an opinion you consider vile or offensive and say, “Well, they’re dead to me,” and remove them. And in extreme cases, I would agree with that. But don’t do it just because you disagree. I have Facebook friends who post things that I strongly disagree with, but it’s important to keep those people around. It lets you see the other side, and see what they see. Know thy enemy, and all that.

15. Don’t Get Into Arguments on Facebook

It solves nothing, it creates more problems than you had before, and it’s just embarrassing. They say the pen is mightier than the sword…but not the keyboard.


16. Watch What You Say on Facebook

You never know who might be watching (the Illuminati, for example). Also, your phone is definitely listening to you. For sure.

17. If You’re On a Date, Only One Person at a Time Can Have Their Phone Out

This isn’t so much a lesson, as it is actually a rule that Abby and I have and I think is a good one to live by. It bothers us when we see couples out for lunch or dinner or whatever, and they’re both just sitting there on their phones. It’s like, you could have just stayed home if you were gonna be like that. So we only have phones out if we are looking up information that is pertinent to the conversation (who was that actor? what time is something? etc.) and the other person can’t pull out their phone at the same time. Keeps us honest.


18. Wine is Best Served in a Mug.

Wine glasses are too scmhancy fancy. Mugs is the only way to fly. And bonus – mugs hold more wine. And double bonus – I have had some mugs of wine while typing this and these are turning less into general life lessons and more into some lessons I have specifically learned but they are IMPORTANT.


19. I Have Come to Terms With the Series Finale of “Lost”

I mean, it took some healing and soul searching to do this, but I have finally done it. Any other Lost fans out there? Were you all about Lost? What did you think of the ending?

*I definitely was never in forums or chatrooms about Lost. Definitely not.*

20. Wear a Charcoal Grey Suit Instead of a Black Suit

It’s much more versatile, is less severe, and fulfills all of the same functions.


21. Singing in the Car Beats Singing in the Shower Every Day

It’s a fact. My car renditions of Hamilton are far better than my shower Sondheim concert. (Abby is right to always tag us #TalentHouse – we never stop singing and being weird theatre people.)

22. It is Possible to Be a Dog Person and a Cat Person at the Same Time

Before Harvey, I never considered myself a dog person at all, but he’s just so darn loveable and snuggly, that I can’t help myself! His little face! He’s so cute!


23. Sleeping With Two Separate Blankets is The Only Way to Share a Bed With Someone

When Abby and I first started dating – she insisted that we sleep holding each other but in two separate blankets. When we eventually rolled or drifted away during the night – no one was left freezing or yanking but there was still plenty of room to snuggle.


24. Autumn is the Best Season

Sweaters, the changing leaves, the coolness in the air, pumpkins, sweaters, it’s just the best, and anyone who says otherwise is just wrong.

25. Lake George is One of the Most Beautiful Places on Earth

I didn’t know it until I saw it. And now I’m positive.



26. Mountain Dew Tastes Better in a Can

I don’t know why, it just does.


27. There’s A Million Things I Haven’t Done (But Just You Wait)

I’ve got 99 things on my bucket list but quitting ain’t one.

There are books I haven’t read, movies I haven’t seen, places I haven’t been, risks I haven’t taken, and in the next 28 years, I’d like that list to have shrunk.



28. Abby is The Best

Ya’ll know I’m going to marry that girl, right?




The next few weeks have some awesome stuff planned! I’ll be doing a post with Eleven60, some fave fall styles, and  as well as more Gwynnie Bee & Society+ stuff, some lifestyle stuff, and more!

If you are at all interested in doing a collab or working with me – please feel free to check out my new Contact Me! page!

I definitely want to do more His & Her fashion. Do you guys like seeing Preston more?

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Comment for topics you would like to see me cover! Like to help my self esteem! What do you think so far? More fashion? More lifestyle? Do you like the mix?

Thank you for all that you do. You are truly extraordinary.

Love all you wonderful ladies (and gents!) out there!

How Very,


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