Sugar Daddy Winter Freestyling Tips

By Brook

Dec 12, 2016

Winter really is the most wonderful time of the year, especially in the Sugar Bowl. There are numerous chances to look like a queen, and to meet a potential Sugar Daddy while doing it. Here are some Sugar Daddy winter freestyling tips.

What is Freestyling?

Sugar Daddies are condensed on SeekingArrangement, but you can also meet Sugar Daddies in real life. It’s not necessarily easy, and does take more time to yield any monetary return. For many Sugars, this presents a unique challenge.

Obviously places like Las Vegas and New York have POT SDs around every corner, but most cities aren’t so fortunate. Which is why the holiday season presents a peak freestyling opportunity. Parties, shopping, errands― the holidays create reasons for these men to be in public. You just have to put yourself out there and have a little tact.

The Holiday Mentality

Sounds of Christmas music and Salvation Army bells remind us the holidays are a time for generosity. Fortunately for Sugar Babies, this time of year is prime for the Sugar Daddy. Men are already in the frame of mind to give, and showing a little extra attention can put you on his nice list.

The holidays are also a time when people feel lonely, especially when they don’t have family or friends nearby. You can fill that void, but freestyling is a “right place, right time” formula. Winter is the right time, you just need to be in the right place.

Venue Scouting

Where do Sugar Daddies hang out in your area? It may take some recon to figure it out. Think golfing, high end resorts or hotels, and classic restaurants. During the other 11 months of the year these can also be places to meet POTs, but the holidays make them heat up.

Figure out the most popular nights and go hang out at the bar. Time it to when the parties are ending, around 11pm. This is a great opportunity to befriend the POTs who went stag and are getting a nightcap.

Attention All Shoppers

The holidays also create many situations for a POT to be shopping― alone. Looking for a gift (for his wife), grabbing a few ingredients, picking up some winter garb. Use your errands to your advantage by looking cute and scheduling some extra time for POT shopping as well.

Eye contact lasting slightly too long paired with a smile is your best weapon here. Once you do have the option to meet what you think might be a POT, you’ll need a game plan to pursue him effectively.

Conversing with Fate

This is a completely fateful and random occurrence… for him. It will be easy to blow it and it will surely not work out every time. If you can subtly (but not too subtly) let him know you’re interested, you can become a permanent part of his shopping or partying experiences.

I have a couple of classic plays for you that work anytime you want to start a conversation.

  1. The Sexy Look – This one is easy, just look at him like you want to jump his bones and let him catch you in the act. Smile, and see what happens. He might talk to you, he might not. If not…
  2. Do I know you? – A perfect followup play for The Sexy Look, and also an explanation for it. “Didn’t I meet you at Gerald’s party a few months ago?” Maybe knows Gerald, maybe he doesn’t. Either way he’ll want to be your date to Gerald’s next event.
  3. I love your [thing] – Get your mind out of the gutter! This is a compliment. This one works if he has an interesting article of clothing or accessory. Say you want to get one for your brother or dad for Christmas.
  4. Can I have your opinion? – This one is my favorite because it implies that you value his opinion, which is a great starting point. Get his opinion on your drink, the cereal in his cart, or the new hockey team in Las Vegas.  

Armed with these conversation starters, you can easily test the waters and see if he’d like to continue speaking to you. After about 5-10 minutes of talking, you can take this to the next level by suggesting the two of you head to an alternate venue.

Shall We?

Research cafes, restaurants, bars, or lounges in your freestyle zone. Asking him to take the conversation to a new location implies you’re interested. He can either reciprocate, or not. The point of this encounter is to get to know him… and his tax bracket. And perhaps to slide in a mention of mutually beneficial arrangements.

Ask if he likes to travel, and where he stays. Ask about his watch, his company or his hobbies. You’ll be able to tell his status by the answers. Once you confirm that he indeed does have the means to be a Sugar Daddy, cut the date short.

Explain you’d love to see him again, and leave him with your number. If you execute this correctly, you should have a second date within the week. A word to the wise: freestyling is all about the long game.

The Long Game

This Sugar Daddy might not know he’s a Sugar Daddy, and you probably want to keep it that way. Start with an expensive dinner. Then try picking a restaurant next to a mall and suggesting you look around after your meal. The key is to act like you’re not expecting it.

After several dates with this unsuspecting POT, you can try some of these ways to talk about money. Overall, freestyling is a time investment, but well worth the long term gains.