skip to Main Content
Tips For Today’s Aspiring Gentleman IV: Women & Dating

Our main goal here at of Iron & Oak is to prepare you aspiring young gentlemen for the grueling world you’ve stepped into. We want you to look good. We want you to live well. And we want you to be knowledgable on a variety of topics. Follow our Tips for Today’s Aspiring Gentlemen and you’ll soon become sprightly, respectable gentlemen in your own right. If you want, pretend as if Mad Men‘s Don Draper and co. are giving you these tips themselves. Not exactly gentlemen, they’ve led long lives full of debauchery, but they’ve learned a lot over the years.

In this series, you’ll find a selection of choice tips spanning several subjects. Some of these may sound familiar, maybe you’re father or grandfather mentioned them to you a long time ago. Some of the may sound completely new to you. Bottom line, we wish we knew some of these earlier on and hope you’ll continue to learn from future gentlemen tips to come. 


1. You don’t have a “girlfriend”. You have a lady, and she should be treated as such.
2. With that said, pick her up, open doors, and offer to pay. Chivalry is not dead.
3. A gentleman doesn’t kiss and tell. Don’t boast your sexual escapades with others.
4. Once in a while, surprise her with a home-made meal.
5. Be yourself, but don’t be creepy. Creepy guys never get the girl.
6. Be dapper, mysterious and adventurous.
7. Develop a sense of humor. Laughter is the key to confidence.
8. There’s a fine line between being flirty and being annoying. Don’t flirt with that line.
9. Leave your XBox alone and play with your lady instead.
10. Go the extra mile by surprising her often.

– – –
As always, if you have any tips to add, comment below or tweet them our way. Don’t be shy. Remember, confidence is key and we’re all ears! Who knows? You may even make the list! Stay tuned for future tips as well as other great articles by following us on Facebook or Twitter. Look Good. Live Well. Of Iron & Oak.

Leave a Reply

Back To Top
×Close search