How To Have A “Vacation Mindset” In Your Own City

Summer is approaching and soon everyone will be on vacation. It got me thinking about how people act on a trip versus their day-to-day life. I see celebrities or just friends of mine posting stories on Instagram and everything looks shinier and special. You are more intentional when you travel; you know it will end soon so you try to cram all the fun and knowledge into the experience. What if you could do that in your own city?

Shop local…..

If you are a shopping at Walmart and then grabbing dinner at a drive-through, you need to rethink your life. I am sure there are wonderful local businesses and restaurants you could be going to. It helps out your local economy and it is better quality. 

There are probably events in your city…..

Sometimes it can get overwhelming to go to every event on the local calendar. You have a mindset of, “oh well, I will catch it next time.” Then you stick to your same routine of staying in and watching Netflix. Try your best to be open to going to events and talking to new people. It doesn’t have to be daily; you can do it once a week. 

Art shows….

Most cities have art openings at local galleries. You will feel cultured sipping on wine and browsing the artwork in a quiet environment. You can also go to a local indie cinema and watch a film.

Local bakery…..

I see all the time that when people go to Europe they have a chocolate croissant and a coffee. Why not do that locally? Take a morning to grab a bite and coffee and then go on a nice walk after.

Have quick hangouts with friends…..

Most people say as adults they never see friends anymore. Why not incorporate grabbing a coffee with friends before you do errands. Even a 45-minute hang is more fulfilling than being too tired to see anyone at the end of the week. 

Changing up your routine will help you meet new people….

The point in switching up your schedule and lifestyle is to get in a new vibration and welcome new types of people and new experiences. It will put you into a more open mindset for change.

You are more free on vacation….

When I am traveling I always think, “I will never see these people again.” So, I have more of a live-in-the-moment sort of energy. Not saying you should embarrass yourself, but you should be more open to chatting with a stranger or getting up and singing karaoke. 

You don’t have to exchange numbers…..

While on a trip you would find it silly to exchange contact info. You enjoy the experience for what it is and keep that memory. Not saying you shouldn’t be trying to connect with people in your town. However, not every interaction you have needs to be repeated. It is good to be in the present moment and not worry about the future. 

Bottom Line…..

Live everyday like you are on vacation. It can really be your choice and your mindset. While we are traveling we have a totally different attitude and agenda of how we spend our days. Every city has local bakeries, restaurants, bars, and grocery stores. We can get in a loop of only spending our time in stressful stores and cheap fast food. An outing can be a simple walk with a freshly brewed coffee or tea. When you open yourself to a more relaxed state of mind, you are welcoming that vibe with different types of people. Practice being braver in public and allow yourself to experience joy and living in the present moment. 

Rewarding Good Behavior in the Courting Phase

Positive reinforcement is a better tactic with any person, rather than negative. Yes, boundaries and limits are needed. You should be stating what you are not ok with. However, as far as everything else, you need to lead with positivity. Praise always resonates more than scolding. How can you reward good behavior in early dating?….

Men always complain about “nagging”…..

Nagging is correlated to a fussy teacher or parent. It isn’t sexy to be called a nag. Even if you feel you are being reasonable and you should express your distain, it will fall on deaf ears. 

Positive reinforcement is feminine…..

When you use phrases like, “ l love it when….” or add in compliments, it makes any person want to repeat the behavior and please you. It is the feminine and relaxed way to get what you want versus being forceful and punishing.

Men rarely get compliments…..

It is expected that he do his job and he probably hasn’t gotten a compliment since grade school. You should express your gratitude if he spends his hard-earned money on you. A “I’m proud of you” goes a long way.

Men who take you on dates versus chatting….

Avoid a penpal by not entertaining it. In 48 hours there should be a date suggestion. Anything beyond that is he being bored at work. Do not reward a man who doesn’t even want to meet you; your time is valuable.

Be gracious….

Don’t expect a guy to pay. If he does pay, he thought you were worth the investment. A sweet thank you and expressing gratitude will encourage him to treat you. 

Don’t make him feel like he is a loser…..

When you brag and boast it will make him feel worthless. There is no need to brag about how much money you make or how educated you are. Focus on the reason why you are dating him, not his shortcomings. It will not motivate him to get a better job or go back to school. Never date potential. 

Bottom Line…..

A thank you and a compliment goes further than you would expect. Most men simply want their efforts to be appreciated. The more you use positive reinforcement the more it teaches him to continue that behavior. You catch more flies with honey than vinegar as the saying goes. No one wants to be scolded or to be punished. He will associate you in a parent or teacher role which is not sexy or desirable. It is more feminine to praise the positive and gives you a gentle energy. Lastly, you will not motivate him to change by bragging about your own accomplishments or comparing him to ex-boyfriends, etc. You can only inspire and put energy towards the positive, rather than the negative.

Why You Need To Let Go Of The “Why”

Women who have been rejected or ghosted always want the reason. They will frame it as closure and maybe a tool to help not make the same mistake next time. However, with women dating men it can come down to a very simple lack of attraction. You can come up with a million excuses, but to men, attraction is the only driving force they have. The best practice in general no matter the reason is to not waste time worrying about it. You can waste months analyzing the text threads and your outfit choices. Let it go….how can you give your brain a rest and chalk the rejection up to lack of a spark?….

You waste time….

It can be disheartening to be rejected or be ignored. You have to understand it is out of your control. It could be he likes brunettes and you are a blonde. Or he was disappointed that you didn’t look like your pics in your app profile. Anything other than him doting on you (buying you drinks, asking you questions, making sure you got home safe) means he wasn’t interested. 

Why app dating will be brutal….

It is so hard to capture an in – person vibe and appearance. Sure, you can do a video etc. but your voice, mannerisms, and your smile are completely different from a 2D picture. You will get more rejections from dating apps or set ups.

“He ghosted out of nowhere!”….

More than likely he met someone he liked better. Men are hunters and will not stop until they find the prize. He probably was keeping you around until he met someone he preferred more.

“Was it something I said?”….

I feel you are allowed one mistake in the beginning stages. You might have gotten too tipsy and chatty, or you said something cringeworthy. He will let it go if he thinks you are worth it. When he didn’t like you that much in the first place, he can place blame on your actions.

Everyone is dating everyone….

Most ghosting and fading is mainly a volume issue. Distance, not aligning, and lack of a spark won’t make the cut. Not to say you are a terrible person or ugly etc. It comes down to timing and having the right fit for them.

Expect VIP treatment….

Going back to how he treats you on dates. Some men will be fine with spending an evening with you. However, he will not offer to buy you any drinks or insists you split the bill at a restaurant. Men show they are invested though money. Keep in mind a good investment to him might be spending $500 at a strip club. And yet $40 on you is out of the question. Don’t waste time on low-effort dates; he is more than willing to spoil the right woman. 

Bottom Line….

A “why” can make anyone spiral. It can hurt to just chalk it up to lack of attraction on his end. Men are pretty simple, visual creatures. All people have a type, but it is important to either delete the apps or be honest about how you are presenting yourself. You will get confused on why he asked you out and didn’t treat you well on the date. It comes down to the physical for men and it is their driving force, versus women who want a great personality first and his lifestyle. Get your face out there in person more and let men approach you. You will know for sure that they see you and find you pretty to them. It can ease your mind. 

The Magic Of The Introduction

We all know about a “setup,” but what if a setup was live in-person? Introductions used to be more common in the polite society of the past. It would be seen as rude when you were not introduced to a new person. I want to suggest the planned introduction, which can be used to your advantage to create your own “spontaneity.” It is in the same vein as “dropping the hanky” technique. How can you orchestrate an introduction?….

Be more social in general….

You need to get comfortable being social and work on small talk. You cannot expect other people to do the heavy lifting for you. Don’t discuss the tragedies in the world and stick to light topics. The introduction will be a lost cause if you lose the person after saying hello. 

Expand your social circle….

Your 2nd- and 3rd-tier friends are the key to expanding your network. Close friends are great, but it is more high risk for you and them. No one wants to cause a riff in their social circle.

An introduction should be fairly breezy and can only be executed once….

Getting introduced multiple times to the same person is madness. Only pull the trigger when you are truly ready. When you have your eye on someone and you know a mutual friend, then plan accordingly. 

To him it can be seen as spontaneous….

The introduction is great because it is not you doing the introduction. There is some innocence to it and it might seem like it came out of nowhere. In the show “How I Met Your Mother,” Barney would make casual introductions left and right to get the ball rolling. 

The introduction can be seen as a “meet cute”….

Any meeting other than a bar and an app is seen as romantic. An introduction, compared to a setup, takes three seconds in person, yet can make a huge impact if it goes well.

Bottom Line….

There is back-end planning for a solid introduction. It can be disappointing if you really took the time to orchestrate everything and it falls flat. It is better to have a policy with friends to introduce you to people at a house party or get- together. To them, it shouldn’t be seen as a big favor, compared to a full-blown setup. You need to do the pre-work of getting your surface level topics in check. The good news is right away you will know his interest level. His continuing the conversation and asking for your number is a great start.

Common Fashion Phobias And How To Combat Them

Why are you so dressed up?….I shudder when I hear that phrase…. most people fear looking too pulled together. On top of that you can trigger criticism from insecure people. This can cause you to dress down and play it very safe to please others. This dovetails into what I call “fashion phobias.” Basically, it’s when you have decided there are certain clothing items that are forbidden. What are some common ones and how can you give yourself exposure therapy?…..

“The Leather Jacket”…..

“I’m not cool enough to wear this.” I felt this way for a long time. I thought it was reserved only for people in a punk band. I finally broke down and bought one at a thrift store last year. My tip is to go with a classic cut. Avoid any studs or dated designs. Mine is simple, and has a tie to cinch the waist. Yes, you can go with a Moto jacket since it does not go out of style, but stick with the classics and don’t buy anything too bulky. 

“The White Outfit”….

“I will spill ketchup on it.” White does not look great on every skin tone. For me, I don’t look good in white since it washes me out. For those who look stunning in white you should not deprive yourself. When you wear all white it gives off a generational wealth vibe. You should wash your whites in bleach to keep them looking crisp. As far as life happening, save your white look for something more upscale. It isn’t a great choice to wear to a BBQ.

“The Heels”….

“I will twist my ankle.” Certain heels are for the brave. You really have to be honest about how balanced you are when you walk. My solution is to wear a block heel. It still reads as feminine and it can ease your mind. I would pick a nude or tan option to streamline your look and make your legs look longer.

“The Tight Dress”…..

“I will look like a sausage in casing.” There is such a thing as too tight, but usually women stay away from anything remotely fitting. Oversize items are a safety blanket and can make you feel you are wearing a magic invisibility cloak. There is a way to wear oversized, but to have everything oversized is not the way to go. Because of Kim Kardashian shape-wear is popular for a younger dynamic. You will feel more confident in a more fitted dress when you have the protection of Spanx or Skims.

“Trendy Jeans”…..

“I will look like I am trying too hard.” Denim can be a good way to try something trendy without too much risk. You need to resist any trend that does not flatter your particular body. That could mean the ultra high waist or low waist, skinny, baggy, all that. A classic for any clothing item is the middle. Not too baggy, not too tight, not too low rise. Sometimes you get lucky and a denim trend that looks amazing on you comes back around. Go with brands like Levi’s or vintage Gap. When you get a flattering cut and wash you will look effortless and not that you are overdoing it. 

Bottom Line….

There was an amazing sketch on “Saturday Night Live” that was titled “fashion coward.” It was women who could only stomach wearing gray hoodies. This is hilarious because it is so relatable. When you are not feeling confident you want to blend into the background, picking oversized plain clothing without any style. You can be discouraged by others when you start to level up your look. They will say passive-aggressive things like, “Wow, where are you going all dressed up!” Resist apologizing for looking good. Say a simple thank you and keep it moving. Having a total fashion overload can be overwhelming. Take baby steps to step outside your comfort zone on your next shopping trip. Pepper in more stylish items with the basics. You deserve to look good and be noticed. 

How To Maximize The Bachelor Pad

Any guy who wants to move the relationship or casual dating to the next level needs a great place. Not saying it needs to be a swinging bachelor pad à la Austin Powers. It is important to present as an adult who has some taste and style. For men who are natural interior designers, this article is not for you. It is a stereotype that men are bad with their living situation. There are too many memes about the “no headboard man / navy sheets dude.” How can a guy curate the perfect “woman magnet” home?….

Location, location, location….

Cannot say this enough. Location is what is going to help you seal the deal. For a man who is living a casual lifestyle, the easier to get to your place, the better. Pick location over the size of the place. You are better off with a studio near town than a one-bedroom further away. Be walking distance to bars, restaurants, coffee shops, etc.

The basics….

Sheets on the bed, plenty of pillows, curtains, two night stands, lamps…. you get it. Not saying you need to splurge at an expensive store. You can thrift lamps, nightstands, and all that. This does not mean your place has to look “girly.” The color choices and fabrics can lean toward masculine. For example, a more industrial style with leather furniture can create a masculine environment. Stick to white sheets or something faintly colored. When you have white bedding they are easier to clean when you throw them all together and use bleach. It gives a hotel vibe that is crisp and clean-looking. Going back to the pillows, you don’t need 50 decorative pillows. You can go more zen and have four functional pillows. 

The extras….

What do you have to entertain with? This is under the assumption that you want a woman to stay over. Do you have a TV with Netflix? Bar cart? Record player? All of these things are nice additions and will give her a reason to swing by. 


Plants are really nice to have around. Not only will it be great for the air quality, but it looks zen. She will subtly think you are capable of taking care of something. Your place doesn’t have to look like a jungle, a few larger and smaller plants around can be a nice touch. You can get away with more bare walls and less decor. 


Art can be tricky to get correct. Unless you are an artist, it is tempting to put up “joke art” from the thrift store. Or have band or movie posters taped on the wall. You are better off with no art if it stresses you out. Even if movie posters are framed (unless they are vintage and arty), it can come across as juvenile. 

Furniture placement….

You are better off with fewer furniture pieces rather than a cluttered look. Many men get inherited furniture from past roommates or relatives. It is important to see what is actually working in the space. The basics are a couch (if you have a living room) and maybe an armchair, etc. Make the space for you especially if you work from home. (Have a desk and things you need). But there should be a place to sit and possibly eat. You can have a large coffee table as a “dining room” table. Most food situations is ordering take-out and watching TV. You don’t need a full dining set up with a table and chairs. Whatever you do, make sure the placement makes logical sense and has a “flow.” 

Dishes, cups, silverware…..

This is again a time where you can thrift a set of simple dishes and some glassware. It isn’t necessary to have a full cabinet, but have at least a few different glass styles available. You will want two shot glasses, a few wine glasses, medium size cups, and one or two coffee mugs. Have the option to offer a drink, even if it’s just water. 

Bottom Line….

A stunning bachelor pad will definitely be a woman magnet. It honestly can work too well, so be mindful with your goals. There are men who do not want women hanging around or spending the night. You can be protective of your place and not bring just anyone there. Have an upscale environment for YOU! It’s not all about being a great host and impressing people. A clean, well-curated home is great for your mental health. You will be able to focus and be more creative. All of these things can be done at a low cost. I always encourage thrifting over buying things brand new. (However, Wayfair is a great option for affordable pieces if there are no thrift options). You can go the route of keeping things minimal and calming with fewer furniture pieces and more plants. Lastly, just because you are intentional with decor does not make your space feminine. It is possible to get a masculine feel by fabric choices and the color palette. Overall, think simple and practical with a little extra. 

How To Hint To Get The Date You Want

When talking about masculine and feminine energy, there is some confusion on date planning. The most masculine way to plan a date is to pick a location, time, and maybe even make a reservation to lock it down. There is a gray area of not wanting to be dragged along on a date, but still trying to come across as flexible. How can the feminine energy person suggest without becoming the social director?….

Speak about things you like….

Be enthusiastic about what bars, cafés, and restaurants you enjoy going to. In the initial “getting to know you” conversation, there will be questions about hobbies and weekend activities. Be specific about certain places you love going to, while still having somewhat of an open-to-explore attitude. 

Your date wants to impress you….

It would be rare if a date went rogue and took you to a bizarre location. A home run-foolproof plan starts with knowing what will impress you. 

Try to be fairly flexible….

You should venture a little out of your comfort zone. Branch out and explore new spots and don’t take every single date to one location. As an alternative it is ok to go to a favorite location before the date to get into the zone.

The 48-hour period….

Plans to meet should be happening sooner than later. Poking the bear after a week, or suggesting you meet up will probably fall apart. Keep the 2-day rule where he can make a plan and you can chime in with suggestions. If a date does not have a time and location, then you do not have a date. 

Try to suggest a fun date if possible….

Not every city has fun activities. (I wish my city would bring back mini-golf.) Cities that have access to a beach or anything that can get you in play mode should be encouraged. You can try your hand at trivia night if you feel you excel in it. 

You can counter the request one time….

He might suggest a place and you are not feeling it. You are allowed to have one counter place that you both could agree on. Don’t get into an argument and make the date planning super stressful. When you make it too much of an issue and can’t go with the flow, he will cancel the date. 

Try not to be greedy….

Do women deserve a 5-star restaurant date with lobster and champagne? Yes. However, you need to focus more of your energy on the conversation and if you can have fun together. Being wined and dined can be wonderful, but with the wrong person you might as well have gone for fast food. 

He is lazy and you want him to step it up….

There will be a case where there is zero effort. He might suggest you come over to his home. In this instance, it is best to go with your standards and say you only do public dates. More than likely he will ghost. Either way, this is better than going along with the bare minimum. 

Bottom Line….

Showing your standards is a great thing. However, when you come off as too controlling, it can ruin the vibe and make him change his mind. You can suggest the type of things you love to do in a breezy way. It is better to say what you enjoy in passing rather than demanding he take you to a specific location. Be realistic about how fancy the date should be. Yes, you deserve a nice date, but keep your expectations in check and go for a middle-of-the-road place for the first meeting. The opposite of this is the bottom-of-the-barrel type date. In this case, you should decline when he refuses to meet you in public. 

Should You Have Unflattering Pics In Your Dating App Profile?

Everyone would rather hear, “wow, you look so much better in person,” versus, “hmm…kinda disappointed.”Give yourself permission to have fun with your photos and get creative. You can have the photos tell a story or have a color theme. This is, of course, not necessary, but try your best to think outside of the box and stand out. How can you lower expectations for your benefit?…..

Use the right filters….

Yes, there are beauty filters, and yes, you will look amazing. I do not encourage you to use them in a profile. You are misleading a guy and it can only lead to disappointment. However, there are filters you can use. I like the “light leak” filter because it does not distort the face, but it gives a cool lighting effect. You can play around with this if you are too scared to have all your photos raw.


I have purchased a tiny beauty “donut” light off of Amazon. It fits on your phone or you can hold it. It will elevate any candid photo. Good lighting is not a crime, but you still want your features to look like you

Go au natural….

A good way to make you look less attractive is to do bare-face photos. You will always wear makeup and good hair on the date, so you will look like an upgrade. It is fine to take a pic with your hair up sans makeup. 

Body shots can be slightly unflattering….

It sort of comes down to what you are most insecure about. If you feel insecure about your body, I would lean into a slightly unflattering body pic. It can be a mistake to kitten fish and show how your body looked like a decade ago when you were on two sports teams and had metabolism. 

Unflattering does not mean boring….

I never think a photo should be boring. You can still make it interesting, but you are not misleading and eventually disappointing. Gym selfies, home bathroom selfies, or car selfies are simply blending in with the masses. You can always make a photo more interesting by the location or lighting. Take an opportunity to do a selfie if you find yourself in a cool bathroom or art exhibit. 

Bottom Line….

With your dating profile, it is better to think long-term rather than short-term. You are better off looking hotter on the dates versus on the profile. It will calm your nerves before the date when you know you will impress rather than disappoint. Yes, you might match with fewer men, but long-term, you are weeding out the highly superficial f*boys. The guys who demand more photos to prove you are “real” should be avoided. They are not interested in your personality or getting to know you. To start out, I would pepper in photos that aren’t glamour shots. Not to say every photo needs to be hideous; it is more about stripping down the photo and making you not look all dolled up. Again, you want to hear a “wow” in person, not a “oh…”

Should You Try Sober Dating?

Bad dating habits are sparked by one too many shots at the bar. One minute you are calm and collected then at the end of the night you are holding onto your heels and calling an Uber. Your dates might feel like a broken record of men shoving you into a casual dating box. If this is happening, it might be a good time to try sober dating. Unfortunately, there are some cons to doing so and some sacrifices. I had a sober period for a seven-year stretch or so and had many first dates in brightly lit coffee shops. (A huge con of sober dating is the atmosphere, usually is not romantic enough to set the mood and tone. I would encourage you to at least meet in the evening to create a cozy environment). But regardless of all that, here are some signs you should give yourself a sober dating challenge….

All your first dates end in a hook up….

Liquid courage can take it a little too far and dissolve your boundaries. You are not giving yourself a chance to let him get to know you.

Men only view you as the “fun girl”…..

“The fun girl” is not exactly a compliment coming from men. It is hurtful since you probably have an education you worked hard at and managed to make a decent life for yourself. Yet all he sees is how many shots you can take.

You launch into therapy mode….

Trauma-dumping and spilling the beans is your go-to. It’s hard to recover from what has been said and you can’t unsay it. It’s tempting to go into intense sharing mode and it ruins your greatest power in early dating which is intrigue and mystery.

Your memory is not at its best….

If you happen to get a second date, you probably don’t remember the initial “getting to know you” conversation. He might accuse you of not listening to him and therefore not caring. 

The good vibes shift into bad….

There are different types of drunks. The worst kind will completely shift the vibe and get angry or defensive. You could start fights or get confrontational out of nowhere.

Safety is not your #1 concern….

Staying safe in any regard needs to be a priority on a first date. You don’t know this guy and also you need to consider a safe way to get yourself home. He might take advantage of your helplessness in a dramatic way or mild way, or you put yourself and others in danger by being careless.

Bottom Line…..

At worst, you are becoming reckless with drinking, but even just giving off the wrong impression can be bad. Listen….. not saying you should never have a classy wine date, etc. My point is if you are relating to any of the signs, then it might be a great opportunity to rein it in a little. We all have different stages of casual dating whether we want total abundance or want to be intentional. Personally, for me, the pendulum has swung to taking a hiatus and regrouping after a year of saying yes to anything. January is the perfect time to reflect and decide what is working and what isn’t. I use the whole month to get focused on goals and to set the tone for the rest of the year. Understand what you are dating for. What are your dating goals? Don’t go by society standards and really figure out what type of dating will work best for you. Or maybe it’s a great time to be truly single and not have all the noise of dating to distract you.

How Can A Guy Successfully Approach A Woman In Public

For a man it’s a tightwire act to approach a woman in public these days. The advice is to just “be a man” and “shoot your shot” while juggling not coming across as creepy. It’s understandable that most men have opted out of any in public interaction and rely solely on the apps. There is however, a wrong way and right way to get a woman’s attention. What are some dos and don’ts to keep in mind the next time you are at a bar and feeling brave?….

Don’t neg….

Listen…. Will it work on insecure women?… Maybe it did a decade ago. It’s so obvious you are doing a move, or you are just not a pleasant person to be around. Look, leading with negativity off the bat is just bad. I get that you don’t want to be the “nice guy,” but negging has a tipping point and will leave the receiver feeling yucky. She will associate that feeling whenever she sees you. Make people feel good in your presence. 

Do make a shared observation….

Great tip is to bond over something. Maybe something funny happened in the bar, or “Cotton-Eye Joe” started playing on the sound system. A knowing smile and laugh shared together is the perfect opening to strike up a conversation. This can only work when you are next to a girl at a bar or waiting in line for the bathroom. It’s not an across-the-room kind of thing. 

Don’t use a pickup line….

Even with self-awareness, it feels cringe. We have heard them all before since middle school. It’s not a hot take to use a “is that a mirror in your pocket…” shtick. It’s not funny enough to be taken seriously and shows you are maybe out of touch or inexperienced. 

Do ask a question….

Steer away from “what time is it”? That can come across as non-specific and not reading as flirting. A good one is asking about what drink she just ordered. Resist talking about appearance because it can come across as an insult. Even a seemingly harmless, “where did you get those shoes?” Could be interpreted as a question of taste not a compliment. 

Don’t approach if she is with friends….

If she is with a gal pal, then the friend will feel a little awkward and the “ugly friend.” It is a little rude to flirt with only one girl in the group. (Not saying you should flirt with all of them). It’s best to approach when she is separated from the group temporarily. 

Do offer to buy her a drink….

I will always accept a free drink, however I know it is buying my time. It is rude to take a free drink and walk away. If she rejects the drink, then this is the reason. The rookie move is opening with the drink offer. You have to feel out the vibe and chat for five to ten minutes. See if she is low on her drink or says she wants to get another. This is your cue to say, “oh, can I buy you a drink?” 

Don’t word vomit….

It’s a balance of flirting without taking it to a vulgar place. It’s best to stay in the polite lane, rather than being overly complimentary (Especially about appearance). This way, she will wonder where you stand about her. She might think it’s just a friendly interaction. The best strategy is to not show your cards. Having her wonder can work in your favor long term if she is interested. 

Do know when to abort the mission….

You have to be self-aware. Nothing worse than not picking up what people are putting down. Facial cues and body language speak volumes. It’s safer to assume she is not interested versus being overly cocky. Be prepared to walk away or not attempt at all based on her vibe or if she is in a large group. The only exception to be a little more forward would be if you are on vacation and have a time limit. 

Bottom Line….

When you land a successful “meet cute,” it will cause a ripple effect of confidence. Most men are traumatized by rejections that happened at the cafeteria in middle school. There is no harm to test the waters and strike up a conversation. A negative reaction could be because she is married or offended by your behavior. Honestly, in certain cases the more a person does not like you, the more polite they become. I end up going into costumer-service mode around people I do not like. Take baby steps instead of aggressively hitting on her. You sort of have to have a “hat in hand” attitude about starting an interaction. It does take practice which can honestly start with chatting more with a bartender or cashier. You need to get used to breaking the ice with strangers without crossing a line. The magic moment is the shared experience interaction which can segue perfectly into a nice introduction.