Dating Advice from the Modern Day Alex “Hitch” Hitchens
The dating bible to ensure you have a shot!
I watched Hitch last night, an old favorite movie of mine. I had an idea pop into my head that they should remake the movie where “Hitch” is a woman helping everyone navigate the modern dating world. While I send this pitch off to Hollywood, I wrote my own version of what I think Ms. Hitch would give advice on. I have joked with friends for years that I would love to be a dating consultant or run a charm school as I have been in the game for so long, and this is my small version of hopefully helping fellow single’s out there.
You do not have to agree with what I have to say, but I am well intentioned as these are things that can make or break an early (primarily hetero) relationship. A lot of people are tired and giving up on dating, and as Hitch says in the movie — you have one chance to get it right. My advice below should help ensure that you do not get on the chopping block over very simple and easy things, though not guaranteed. And just as the movie, my target audience is for people who are emotionally available, dating intentionally, and searching for love — not for people who are dating very casually. I hope you enjoy!
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Phase 1: Matching with Someone and First Dates
Do not form a strong opinion about their personality before the date
A lot of people curate their dating profiles based on how they would like to be perceived rather than how they actually are in real life. People can be completely different from their texting style, pictures, and even responses to prompts — so do not get too attached to them and jump to conclusions. You should vet them at least a little bit, but do not fantasize and form a clear idea in your head of what they are going to be like — you are going to shortly find out on the first date!
Vet someone before the date
Some people let themselves down before even going on the date by not actually processing someone’s dating profile and messages. There are plenty of edge cases where opposites attract and very different people can fall in love, but for a lot of you — alignment in core values matter. You do not have to message that much prior to the date (I will normally only say a few sentences until a plan is made) — but I found out as of recent that some people do not even fully look at a profile. I acknowledge that some people lie on their profiles, but if politics, religion, location, job compatibility, height, relationship intentions, pets, or even zodiac signs are absolute dealbreakers for you — do not overlook it!
Figure out what is high priority and what is low priority to you before the date
Some people like to utilize the first date to get to know someone (and that is totally fine), but I have a knack for reading people quickly. It entails asking the right questions to figure out if this person exudes core qualities that are a preliminary match. When someone is serious about dating, not wasting time is a top priority (and it benefits both parties). A great theme to start with is — what is important to them?
A lot of people lead with physical attraction because it is the main component you see in a dating profile, but the next step is figuring out what qualities you value, and anything that might come with it (the often overlooked part). For example, if you want someone who looks polished, put together, and clearly invests time and money into how they present themselves — then you also have to respect the dedication, time, and effort that they are putting into it.
And if this is clearly something visibly important to them, then you should probably assume they are looking for that same respect and investment with you. If this is a low priority for you, then you might want to find someone who also has it as a low priority (this has nothing to do with level of attractiveness, by the way). This does not always have to be the case, but the respect of the process is important. You do not want someone constantly making you feel bad about the time and effort you take to look and feel good!
If you are looking for someone who is very smart and passionate about their work, then you can probably assume that they themselves want someone they are able to converse with and should also respect all that comes with it — perhaps long hours working on their passion, time investment in reading and learning, and a mutual respect on the ability to grasp complex topics.
Again, maybe you know nothing about what the other person does or what it takes — but you have to respect it and at least make mild efforts in seeking to understand. You definitely do not want someone who looks down on your job or interests, acts completely uninterested, or is not okay with long work hours if that is your current state in life. If you are not willing to respect it, perhaps it becomes a lower priority over another quality.
These things will become transparent if you notice they are only talking about themselves, versus providing a good balance of asking you questions. Also, a good indicator of a respectful person is not only how they respect you and your views, job, lifestyle, and passions — but also how they treat and talk about people that they may not align to or be as attracted to. Unless you are a hundred percent aligned on sense of humor, stray away from offensive jokes or comments for the sake of getting a reaction out of them — you may not know what is near and dear to their heart.
Be a planner, date intentionally, acknowledge safety concerns, and respect each other’s time
Yes, a lot of people will agree to a poorly thought out plan — but that does not mean that it is okay or should be the standard. If you are dating intentionally (and you really want to impress her), imagine you are going over your plan with her parents or even your parents — would they approve of it? If younger people in high school can easily do the below, so can you.
If you are asking a woman out, respecting her time means asking for her availability well in advance (at least a few days but a week is preferred), asking about any preferences and/or food allergies, and providing the option of drinks or dinner — this shows that the effort of dinner is made, but also makes her feel safe and comfortable if dinner is too risky for her. Believe it or not, there is a big percentage of women nowadays who will not even accept a date or ghost someone if they do not plan on a dinner date — it is the principle of putting in effort in pursuing her.
If she chooses dinner, make a dinner reservation at a reasonable time for her to have time to get ready (7:45/8PM is the sweet spot - at least in LA), and confirm a plan on how she is going to get there. You need to offer to pick her up or call her an Uber even if it is out of the way. She does not have to accept if it feels unsafe for her, but you should always offer and take baby steps in creating trust where she can rely on you to get her safely from Point A to Point B. And a lot of women love being a passenger princess!
The date does not have to be dinner, but at least provide options such as coffee versus brunch. Some women will align to a more low stakes date for safety reasons, but you want to make sure you cover all the bases in case she is looking for a man who puts in effort. I am really basing this blog on Hitch — and if Albert were wanting to pursue Allegra Cole today, he would still have a shot with this plan. Other ideas could be a concert, sunset picnic, fun activity like cooking or pottery, or some type of local event (some popular ideas I have seen with close friends or experienced) — but make sure to provide options.
Communicate the plan in advance, and make sure to confirm the plan on the day of the date (the earlier in the day, the better). Try to look presentable (please no sweatpants or running shoes), show up early (if you planned it, you should try to avoid arriving late), and take care of the bill. A quality date is not about a single component, but the full follow through. If you plan on splitting, make sure you communicate this before the date — as many women will have the assumption that if you asked her out, you plan on taking care of her. Some women do prefer to go 50/50, but you should both be on the same page prior to the date to prevent misunderstanding or a bad ending to a great date.
No matter how the date goes, prioritize her safety always and offer to get her home by dropping her off or calling her a car. She does not have to accept, but the offer should always be there. Even if she is driving herself home or taking her own Uber, offer to walk her to the car and open the car door for her — this is true chivalry! Make sure to check up on her to confirm she arrived home safely. Men often do not realize how much of a safety risk a woman takes just by simply going on a date or getting into a car. If you do not see a connection, send a quick text that you had a great time but do not see a romantic connection.
Modern dating has made this out to be on social media as hard to find, when it is truly so easy! If you needed any validation that this is baseline treatment, you are not crazy for requiring this. Most of the people I have dated have done all of these things without a second thought — no matter the level of casualness or outcome of compatability in LA of all places, so this is my proof that it exists.
Phase 2: The Courting Phase
Know your worth, be authentic, and have self-confidence
This goes for both parties, and is crucial to preventing self-sabotage and turning off the other person. Coming from a woman’s perspective, attraction comes from effort and consistency — not looks. If you have the mindset that the person you are dating is completely out of your league, odds are high that you are going to sabotage the situation. This does not just apply to looks and status — this also goes for people with anxious or avoidant attachment who have not done the work to figure out how to participate in a healthy relationship. In these cases, some people self-reject and sabotage because the other person is “too good” or “too ready” for them.
Everyone has beautiful qualities to them, but not everyone has taken the time to acknowledge their self worth and own their power. If someone has agreed to go on more than one date with you, that is the only validation you should need that they enjoy your presence.
You should never try to act like someone you are not just because you think that is what the other person wants. People are easier to read than they think, and your quirks are what make you uniquely you — and probably something they really like about you rather than something you should be hiding. Most importantly, do not dim someone else’s light for the sake of bringing them down to a level you are comfortable with. In that case, please have some self awareness and step away.
A good question to ask yourself is if you lost all of your friends and family and were not in as great of a place in life as you would like to be, could you still look in the mirror and love what you see? If something does not work out in your favor, are you able to have self-compassion and acknowledge growth opportunities rather than projecting onto others or blaming other people/the world for your problems? If you can answer yes, you are ready! If you need a little more time, I suggest therapy or therapy books, getting comfortable doing solo activities or going to dinner solo, and practicing positive self talk. Being in a relationship can hold up a mirror to your triggers and insecurities. You want to ensure that you will not blame the other person for all of your problems, or become jealous of their accomplishments and the amount of attention they get!
Also, make sure that you do not become entirely dependent on this person for your happiness — they may contribute to it, but it should not be their core responsibility! This puts too much pressure on them to fulfill every single one of your needs and every bucket of your life — and may create a very unhealthy dynamic. It is important to still own your authenticity and make time for platonic friendships, family, personal hobbies, and your own goals in life. If they are not available for something you want to do — you should not take it as rejection, and it should not be the end of the world!
Also, have confidence in who you are as a unique person and fully participate in the relationship to co-create what works best for the both of you. An anxious-secure relationship will look very different from an avoidant-secure relationship — and you should never compare them! It may be helpful to identify small bits and pieces from relationships you are around that you would like to have in your own. But remember, you probably do not even want that specific relationship or carbon copy of that person. Focus on yourself and finding exactly what you are looking for!
Reflect on why you like them
This may seem bizarre to some people, but a lot of people date and do not actually truly like the other person. So, what do you like about them — and do you actually know them well enough? If your answers are more surface level (looks, lifestyle, popularity), stuck on the idea of being with someone or in a relationship with anyone (some people do attach quickly to the first person who has given them baseline/proper treatment or attention), or solely based on validation or getting validation from others just for dating this person — odds are that you have not gotten to know them and do not actually like them as a person.
Often times this may be lust or limerence instead, and it is important to know their difference from like and love. I deeply empathize with people infatuated with someone who made them feel special and seen, but you have to ask yourself — “do I actually really know this person or am I attaching to a singular memory or interaction with them?” Odds are, that person is a completely different person now versus the memory you are attached to, or not at all what you have fantasized in your head. Also — take people for face value rather than falling for their potential, or even the potential that you envision for yourself just by being with that person.
If you are okay with dating for one of the reasons listed, fine by me as it’s your life — but I personally recommend that people choose to date someone because they actually like them. By knowing what you like, you can actually consider who would be the better long-term partner if you are dating multiple people, or what sustaining qualities fulfill your specific needs. I acknowledge that men today may have the misconception that women solely prioritize lifestyle — but if she has had experience dating these types of men she will know that a large majority are emotionally unavailable, and the relationships are primarily short-lived. If she is actually looking for a serious long-term relationship that meets her emotional needs rather than a purely transactional relationship, she will most certainly be looking beneath the facade for genuine qualities. On the flip side — if you are a man who is interested in a deep connection and values having a beautiful woman by your side, make sure you validate the non-surface level qualities you love.
Communicate your needs early
Communication issues can lead to misunderstandings, fights, and even the end of a courting phase or relationship. Unfortunately, most people cannot read minds. Knowing the below can’t solve everything, but are at least great baseline questions to communicate your needs effectively and prevent some mishaps.
How do they like to stay in touch when you are not together? Do they prefer calls, facetimes, all day texting, once a day texts, or love letters by carrier pigeon (I’m only half joking about this one). There should be absolutely no confusion on when you are hearing from the other person, or when you are going to see them next. If you have not learned by now, “butterflies” are actually anxiety most of the time (I know, I too had to go through the 5 stages of grief to accept this). You should not be nervous about someone liking you, and you should not even want someone who is not showing through actions that they are interested in you. Remember — consistency and effort is key. For avoidants, this consistency may come off as boring and the “safe option” — but it is actually simply your first healthy relationship!
What is their attachment style? As a general rule of thumb, if you are dating someone with anxious attachment — more frequent reassurance is needed; if you are dating someone with avoidant attachment — prioritizing their space and independence is important. If you are dating a primarily anxious woman, be generous with your time, respond right away, focus on building trust, be comfortable giving compliments frequently, and be transparent about female friendships to avoid jealousy. If you are dating a primarily avoidant woman who has been independent her whole life and taking care of everyone around her, it will be key to proactively do things as she will rarely ask for help (but secretly she wants it, and will be so appreciative), and be supportive of her alone time.
What are your “ick’s” or red flags about them? Obviously do not fire these off one by one or send them a screenshot of your list, but the intention is to not throw away the person if these things are solvable with some direct communication. This should be a two-sided conversation so that both people’s needs are being met.
Approach these conversations in a delicate, yet firm matter that these are things you require in order to continue with the relationship. If these things are core values, unsolvable with communication, or voiced and met with unwillingness, then do not force it! Acknowledge that there is some misalignment with compatibility, and there is someone out there for you that is a better fit.
Also, please have empathy and acknowledge that bringing it up or having to ask for it may be uncomfortable for that person, so if it is fixable make sure they only have to ask once. There is also a balance of how many things are worth communicating or asking for versus what should be done or known without having to ask on principle. If the list becomes too long, the other person may end the relationship based on incompatibility so as not to completely change you as a person.
Have an actual conversation when 10-12 dates have passed and you want to date exclusively. Yes, there is a difference between dating exclusively and becoming “boyfriend girlfriend” or being in a committed relationship — so there should be two conversations. The timeline may be faster or slower depending on your specific situation, but this should be a general rule of thumb - do not assume! If you really want extra points, come up with a cute gesture and ask “Can I be your boyfriend” instead of “Will you be my girlfriend” - this is majorly swoon worthy!
Fix your relationship with work
This is the one that I have the most trouble with, but you have to prioritize and pursue a connection even if you become overwhelmed at work. No one is forcing you to choose between work and a relationship, yet many people often sacrifice one for the other. I acknowledge that it is hard when other coworkers are already married with families and have a stabilized routine, but it is not impossible to set aside a few evenings a week to date — or take a few moments to respond to a text. As long as you communicate early and often when you are having a busy week, when you are running late, and when you are in a stressful mood — the right person will be understanding and even help make your life easier.
Now, you should not normalize these types of things — but also do not suddenly decide the relationship will not work because of a demanding project you are on (trust me, I have made this mistake many times in the past). And definitely do not think of your time as more valuable than another person’s — or that your occupation or work is of higher value than someone else’s. Even if they do not work or have a schedule of leisure activities, they do not owe dropping their plans to accomodate yours. If you are someone who projects your stress onto other people — you definitely need to resolve this first before dating.
I like to keep my work stress in a controlled environment, and affirm myself constantly that no outside factors or relationships have anything to do with that stress (i.e. make sure that your mood is not impacting someone else’s mood). Maybe you require a different strategy, but you should definitely have one. If your work keeps you busy constantly, you may want to focus on finding someone with a secure or avoidant attachment style — as an anxious attachment style may require a lot more time and energy into validating the relationship. If you face this problem frequently, focus on ensuring that you are respecting the other person and their time.
It is interesting to me that I have had many deep conversations with men about career over dating (and also have seen similar sentiment on the internet). It seems like they have the mentality that they have to be at a certain point in their career and have everything in order before dating. It is very much a chronological order, prioritization mindset — but you should not dismiss a high potential connection just because you have not established yourself enough. Remember — the odds of a mutual romantic connection are rare, and you do not want to regret “the one that got away”! This will differ by relationship, but a lot of things can be understood and worked on — at least voice your concerns before self-rejecting. It is important to practice emotional intelligence and relationship building over time, not just when you feel the time is right — or else you might not be ready from an emotional standpoint when you finally meet someone amazing.
Small things are actually really big things
I think that a lot of men out there are unaware of how much women notice the really small things, sometimes even more than the big things. This may include the following:
If you want to pursue this woman seriously, pay for the dates and if you want to be really suave — pay beforehand or hand over your card while going to the restroom to avoid any awkwardness (I mean I even do this when treating friends or family)
I know this is a controversial topic on social media, but as Hitch would do — this advice is for seriously pursuing someone you are very interested in — and will ensure that she does not ghost you (as what a lot of women would do if you asked to split). Again, you do not have to agree; I am simply ensuring nothing is counted against you!
Open doors, follow the sidewalk rule, and confirm safe arrivals — a.k.a. make her feel safe and secure with you!
Women take a big risk in terms of safety by simply going on a new date and even getting into Ubers — so it is important to create a safe and secure foundation in the relationship. Do not just pick her up or drop her off in the dark, but also confirm that she got in safely and/or double confirm that she arrived safely even if you tracked the Uber that there was a dropoff.
She will notice whether you walk around and open the car door for her, follow the sidewalk rule, or pull her seat out at a restaurant — these things can be even more memorable than the planned date itself! And she will definitely notice if there is a loss of consistency with these things.
Do not force anything and respect her boundaries
This goes without saying, but do not pressure her to stay longer on a date than she would like, or force any acts of affection unless she wants to. The first few dates need to be focused on building trust! Do not make her repeat her boundaries, as this will make her feel unsafe — and you will probably never see her again.
Look presentable
You do not have to go crazy and buy a whole new wardrobe and hire an extreme makeover team, but show at least a little bit of effort. You would not want her to arrive to a nice restaurant in sweatpants, sneakers, no makeup, and unbrushed hair (though I acknowledge men love this in a casual indoors setting) — so make sure you commit to what you are requesting of her. This varies by woman, but I personally will take 2 to 2 and a half hours to get ready for a date — not to mention the frequent beauty maintenance appointments. Rule of thumb — make sure your shirt is not wrinkly, put on real pants, brush your hair, cut and file your nails, smell at least neutral or nice, and groom your scruff or beard if you have it. This should really only take less than 10 minutes in comparison to the time she is investing in the date!
Create convenience
You will never know the kind of day she is having, so respect the time she is committing to the date and create convenience so that she does not have to think extra hard about going to the date. Even if it is annoying, go out of your way to show that you value her time.
Thoughtfulness in small ways
Thoughtfulness comes in all forms, but the most memorable will be the small acts. This could be remembering her favorite snack and bringing it for a car ride, picking her up from a workout class or work with her favorite drink, going the extra mile if she is sick by bringing her or sending her soup and ice cream, treating her to a new lipgloss, or sending her flowers when she has had a bad day. These small things truly make the greatest difference — the key is to do it without asking! P.S. In order to do these things, you need to take interest in her preferences (food, drinks, ice cream flavor, color, and flower types). Doordash/Postmates is the modern day carrier pigeon!
Be romantic and vulnerable
This one pairs nicely with bullet #1, but if you can truly see yourself with a person — you need to be all in! In my personal opinion, this is the stage where things go wrong. Some people may be nervous that it will not work out, so start to put less and less effort in just in case it does not work out. Or, they put in minimal effort in general in order to juggle dating multiple nights per week. People often forget that before the talk of exclusivity, most people may be going on dates with more than one person — so just because the last date went well, does not mean you have got it in the bag. Odds are that if you think the person you are dating is exceptional, other people do too — and will do absolutely anything for their time.
Being vulnerable can be scary for both parties, as there may be a past of traumatic endings to relationships or long situationships with no commitment. But, it is important to talk about not only the good, but also what your emotional needs are — this could be insecurities, mental health, relationship with family and friends, or current challenges in life.
To kick off a deeper conversation, here are some questions and phrases that you can use instead of the generic ones that tend to brush over how someone is feeling: 1) instead of “sorry you had a bad day” say “how can I make your day better”, 2) instead of “you will be fine” say “I am going to help you through this”, 3) instead of “I don’t understand” say “please help me better understand your perspective”, 4) instead of being frustrated, confused, or unresponsive — say “thank you for voicing/sending this; let me take time to process it thoughtfully before I respond”, and 5) taking feedback about hurtful behavior in a positive manner such as “I know xx is not a strong suit of mine, I am going to work on it”.
If directly asking uncomfortable questions makes you nervous, there are a lot of fun and engaging activities that can help facilitate these conversations such as ‘We Are Not Really Strangers’, ‘The { } And’, ‘Unpack That’, and ‘Bold’. The game does all the heavy lifting for you! They are also great activities in general to get to know someone better.
It is important to identify whether this is a person who can support you and lift you up when you are feeling down or in a complex situation. For example, does this person avoid talking about their feelings or make light of a tough situation? Some people need someone with a sense of humor, some need a problem-solver, some need a motivational speaker, while others need someone who can deeply empathize and validate what the other person is feeling. It is important to know whether someone is looking for an actual solution, mood booster, or validation of how they are feeling. This may also be a source of identifying incompatibility with emotional needs.
My personal biggest indicator as to whether someone is good for me or not is reflecting on if they help to make me a better person. This may be seen with my mood, home environment, consistency of taking care of myself, motivation towards my goals in life, and growth in healthy communication. There may be some off days, but the theme overall should be that this person provides emotional safety and challenges me in a positive, healthy way. Even when I first meet a close friend’s new relationship — I am focusing mostly on my friend’s body language and sense of security to assess whether it is truly a good match.
And now — getting to the good stuff. I am going to put this section in bold because I think it is the most important paragraph of this blog. There is too much confusion on the internet about “lovebombing” and being a “simp”, versus being romantic and intentionally pursuing a romantic relationship. “Lovebombing” and “simping” is when you are trying to excessively distract someone from your poor intentions or motivations through attention, gifts, and empty promises.
Blurring the lines with simply being romantic and developing feelings for a woman where reciprocation has been received is having a destructive impact on the modern dating world. Sometimes it just takes practice for women to identify the difference, but men should not be scared to share their feelings or do romantic acts out of pure fear of being labeled as this. Also, being romantic can only help your cause — and any friends teasing you are not your true friends. True friends are going to be your wingmen and help and support you to win over your once-in-a-lifetime love.
From a woman’s perspective, being romantic will be shared with her friends — and trust me, you want to win over her friends as they are in her ear with every step of the dating journey. If you really do it right, they will swoon and it will spread through every network that any woman would be very lucky to date you. If you are not being thoughtful, considerate, or putting in extra romantic effort — you will be met with a lot of friction if you do end up being introduced to her friends and instead of praise, warnings will be spread around.
And let me emphasize if there is still any confusion, women want to be courted and woo’ed. We have been fed RomComs and fairytales our whole lives — and if she reads a specific genre of romance novels, let’s just say that you better kick it up a notch if you want to win her over. So send or bring her flowers every couple of weeks (even just a single rose stem), bring her a favorite smoothie or coffee, book that restaurant with candlelit tables, cook her a nice dinner, write her a little note or love letter, book a couple’s massage, or drive her to watch the sunset.
If you think these are too cheesy, there are plenty of men out there who would do anything to do these things for her and make her smile. And women, do not let anyone convince you that you are not deserving of these things! If you are dating a woman who has been happily independent for a longer period of time, you are most likely not competing with other men — but rather her peace and standard of life being single (hint: her life should not become worse with dating). If you know for certain that you do not contain a single romantic bone in your body — please stay away from women who are sentimental, believe in true love, watch RomComs frequently, read Romance novels, and do thoughtful little things without asking. You will need a woman with lower requirements in the romance department.
When I think about someone finding “the one”, you will be able to say that you did everything in your power with no regrets. As Alfred Tennyson wrote, “Tis better to have loved and lost than never to have loved at all”. Both parties have to be willing to take the risk, even if it ends up not working out. If you find that you have a big fear of rejection, try doing rejection therapy before dating someone new. I have unintentionally practiced it for years, to the point where my outlook is sturdy in the mindset that any rejection is redirection, and everything happens for a reason. No love is wasted or lost through a platonic or romantic relationship no matter how short or how bad it ended, as there is always something you learned.
5. Be empathetic and kind
This should go without saying, but everyone is going through tough things and it can be easy to harden and be pessimistic when you are surrounded by other people who carry this type of energy. Choose to be kind! You do not have to like everyone, but at least have empathy and treat them like a person. If you do not see something working out whether it has been one date or 12 dates, have the courtesy to send them a text as soon as you have made your decision instead of ghosting. If you have been exclusively dating or in a relationship, a call or in-person conversation would be the preferred route as at that stage you have built a deeper connection. And if you are on the receiving end, also have empathy and be understanding that this was probably a tough decision that took a lot of thoughtful consideration — it is not easy for either person. If you are met with a bad response or no response, that is even more confirmation that the connection was not a match. Remember — confusion is closure and every person processes their emotions differently!
6. Keep going
The end of a promising connection or relationship can be devastating, but please do not let it hinder you from putting yourself back out there. I of all people know what it is like to be single and dating for a very long time span, and it can be hard to not “settle” when you are tired of the process of dating. Try to ignore all the comments that “it will come when you least expect it” — these people mean well, but the most important part is that you have dated enough and done self-reflection to know what your triggers are, what your needs are, and what your wants are.
I have learned so much about myself over the years, and with each person you only get closer and closer to what you are looking for. There are so many people in this world, and you have not even met the people who are going to completely change your life. Remember that you are beautiful, special, and deserving of love — and your person is out there searching for you, do not give up on them! It will all be worth it in the end.
I would love to hear from you if you enjoyed this blog and would want it to be a series. As stated in the introduction, I have joked with friends for several years that I would be great at being a dating coach or running a charm school, so this was a really fun one to write! Cheers to new connections, love in all forms, and the revival of romance!
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