Questions tagged [awkward-situations]

For questions about situations which are awkward for anyone concerned. This tag should be used when awkwardness is the key part of the problem.

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25
votes
5answers
58k views

How to contact a girl whose number I got from somebody else?

Situation Some days ago I went to a concert of the band of a good friend, let's call him Alex. He and his bandmates, invited a lot of friends to support them. I know Alex pretty well since we've been ...
38
votes
4answers
18k views

How to approach a friend about his girlfriend asking to sleep with me?

Context My girlfriend (let's call her Claire) shares a flat with a couple (let's call them Bob and Alice). Bob is a close friend of mine, and I get along pretty well with Alice. The three of them used ...
11
votes
2answers
835 views

How to gently and compassionately stop a stranger talking to you about their problems?

I recently dropped my wallet while shopping, reached out among local lost-and-found groups on Facebook, made contact with someone who found it and made arrangements with them to meet up so they can ...
97
votes
11answers
63k views

How to respond to someone when they ask how much you earn? [closed]

When I'm at social gatherings/parties, people would inquire about my job and, because I'm an app developer, they think I earn substantially more than I do. (Oh, the joy!) They then follow up asking ...
13
votes
3answers
4k views

Asking an ex-girlfriend out to coffee, now that she's married and has a child

One of my closest girl friends that I dated for a while - and then remained close friends with even after we decided to just be friends - got married over the past two years and also just had a baby. ...
30
votes
5answers
23k views

Same Gender Friends-with-Benefits [closed]

Context My friend and I are straight males and we both have girlfriends. We have been friends for quite a long while, and there are a few occasions where we've talked about friends-with-benefits (...
3
votes
2answers
649 views

How would one greet a person on his/her birthday today, especially when his/her father died yesterday?

How would one greet a person on his/her birthday today, (at least some sort of greeting to acknowledge his/her birthday) especially when his/her father died yesterday. I am from Sri Lanka and he is ...
5
votes
2answers
3k views

Handling awkward situations caused by morning erection around non-romantic partner

I'm an 18-year-old male. Some weeks ago, I and a female friend of mine went on a one-week cycling trip. We're almost exactly the same age, she's an old childhood friend, we've known each other ...
110
votes
17answers
25k views

How to let tech support subtly know that I am proficient without showing off?

I manage a couple of small websites for friends and family as their admin, ranging from installing wordpress to full-stack web development. In this position I often have to contact the support of ...
1
vote
1answer
544 views

Is it unwise to attempt to anger other drivers who are exiting the highway? [closed]

There have been many times while driving on the highway when another car has suddenly cut into my lane in order to get over to the right-most lane so they can exit the highway, and I had to slam on ...
4
votes
4answers
783 views

How to have a casual conversation with new colleagues?

I've recently started working with a new company, and it's great. Every few months, they'll organise for everyone to meet-up in a pub after work for drinks. There's a meet-up coming soon which I'm ...
2
votes
2answers
398 views

Accepted receipt of ‘deepest sympathy’ flowers for neighbour

I recently accepted receipt of some flowers for a neighbour who wasn’t home. We don’t know the neighbour at all (even to say hi on the street). The flowers are clearly for a death in their family. ...
6
votes
3answers
3k views

How to Deal With Asking Out A Friend's Sister

I've been friends with the oldest brother, Gary, since middle school. His younger brother Billy also integrated into our group of friends around high school and Billy, Gary, and I frequently played ...
85
votes
8answers
59k views

How to reject a proposal from a close friend?

I have been friends with a girl at work for more than a year. I have always seen her as a friend and I am pretty sure I never did anything to lead her on. I am going to switch jobs in a couple of ...
2
votes
2answers
7k views

How should I approach my crush if she's not interested? [closed]

TL;DR: There's this girl I really like, who is apparently not interested in me, since I've already made a move on her without any luck. Nevertheless, I've decided not to give up and make one more ...
2
votes
0answers
350 views

How to deal with a frank speaking and overthinking guy [closed]

I am hanging with a group of friends all around 22 - 23 years old . One of us is sometimes having some anger and sadness at mixed times. It makes the group feel weird. To detail these crises: he ...
2
votes
2answers
596 views

How do I get a second opinion without offending my longtime dentist?

I have been going to my dentist for the past 18 years. It's a family practice: the dentist, his wife (hygienist), his sister-in-law (appointments and billing), and some additional staff I've never ...
10
votes
3answers
876 views

How do I politely/non-awkwardly get to know/give my number to a woman on a bus, in a non-intrusive manner?

So the title already gives some major details, but I’d like to evaluate further, to explain the situation better. I’m currently working on a short-term job, ending next week. The commute to this ...
13
votes
4answers
2k views

How to approach my Boyfriend on his opinion about having children eventually?

I've got a wonderful boyfriend who I can very openly communicate with. We've been together half a year, but we've been friends for years before that. I'm in my early twenties. So far we have handled ...
36
votes
6answers
13k views

How to inform guests when you don't have enough food for everyone? [closed]

Background I volunteer as an apartment group leader at my apartment complex. Every Monday, I'm in charge of organizing an activity (up to $20) for my fellow roommates and neighbors. Recently, we had ...
4
votes
2answers
714 views

How to encourage people to not make/cancel travel plans based solely on my personal opinion?

I live in a city in the UK that is hosting some competitive sporting events in coming months. From my time at university and beyond, I have made a number of friends and acquaintances across the globe, ...
6
votes
2answers
1k views

Address friends overly “agressive” way to get attention back on him when around girls

I often go out on weekends with a few friends of mine, we're all around 18-21 years old from Germany. One of them (lets name him L.) really is a chill guy. Me and my friends aren't really that good ...
-1
votes
1answer
446 views

How to tell someone you are pregnant at such a late stage? [closed]

I am 35 weeks pregnant and I didn't tell an acquaintance of mine yet. She is an old co-worker of mine and works a few blocks away. She quit working at the same company as me in January. She was ...
14
votes
4answers
7k views

How to turn down unsolicited advice at the gym? [duplicate]

I'm going to the gym quite frequently, so does the guy this question revolves around. I don't really like chit-chatting (or talking in general) while im working out - I'm usually in my zone, with ...
7
votes
6answers
2k views

How do I politely say no to a stranger asking to use my phone to make a personal call?

TL;DR A stranger approached me and asked me if they could use my phone. I didn't want to be rude and say no bluntly, so I wavered, and felt uncomfortable. How do I say no to strangers asking for use ...
71
votes
14answers
30k views

How do I respond to racist remarks from a coworker?

Recently, I've had a couple short conversations with a coworker that have taken a racist turn, and I'm not really sure how to respond. We don't work directly together, but often see each other in ...
13
votes
2answers
773 views

How to deal with friends finding out I self-harm(ed)?

I have a slight situation arising and would like some opinions/thoughts on how to proceed. Some Backstory I am male, in my early 20s. I have self-harmed for a number of years, and am currently a ...
5
votes
2answers
688 views

Politely recommend budget help to a friend who owes me money?

To address duplication concerns, this belongs on IPS rather than workplace stack exchange or finance, as I would like to address the specific issue of recommending budget help, and handle this as a ...
2
votes
2answers
482 views

How can an English teacher tell their student that the student is dyslexic?

An English teacher working in Russia notices that their student has adequate speaking and listening skills for their level, but really struggles when it comes to writing and reading, both in English ...
15
votes
6answers
21k views

How to convey (non-awkwardly) that its my birthday? [duplicate]

First off, I know that this question is very close to mine, but has no answer that would match my needs. Secondly, I find it shocking how many people answer for a workplace situation. This question ...
24
votes
4answers
4k views

How can I decline to help my teacher with their personal IT problem?

Background Note: Certain details have been changed for privacy's sake. I am the go-to person for tech help for my friends (and enemies), family, and teachers. I have helped everyone I know with ...
15
votes
2answers
983 views

How can I estimate the length of my responses or reactions to avoid wasting others' time?

I often notice for myself, as well as for certain other people, that depending on personality and some other subtle factors, there are types of people who (usually unintentionally) start over-...
8
votes
2answers
2k views

How to tell an artist friend that their art has been getting worse if they think otherwise

Not long ago, a friend of mine got some rather harsh and even somewhat rude criticism, anonymously, that their art has been regressing for a while and that they're squandering all of their potential. ...
12
votes
3answers
2k views

How to decline eating food at a restaurant?

I'm often invited to restaurants before or after certain meetings with groups of people I know, including friends. However, I don't like to eat "outside food" and never go to restaurants or get take ...
8
votes
1answer
679 views

How to talk to someone about work after their significant other passed away

I recently moved into a shared home where my landlord is one of the roommates. Shortly after her husband passed away. Understandably she’s been upset and stressed. Also I was told it was the husband ...
17
votes
5answers
12k views

How to ask a neighbor if I can replace our shared fence?

I recently moved into an older home with fences between my home and my neighbor's home. Based the way the fences are constructed, I believe that they are owned by the neighbors and not myself. One of ...
5
votes
4answers
1k views

How to win a game without hurting someone

A few months ago, I joined a chess academy which divides its members into groups of ten for the sake of coaching them efficiently. Mine had eight men and two women with ages ranging from twenty to ...
22
votes
5answers
8k views

Attending the 9/11 Memorial next month - how to interact with families that lost loved ones?

A couple of us are planning to visit the 9/11 Memorial in New York next month on September 11th itself; it would be our first time visiting the memorial. I want to be careful to not treat the event as ...
3
votes
1answer
861 views

How to approach a random person that appears to be interested in you?

A lot of the time (3-5 times a month) when I'm walking in the street or sitting on the public transit random strangers will make eye contact with me for more than 3 seconds and also smile at me in a ...
16
votes
3answers
6k views

How to resume contact with a former manager who I haven't talked to for 3 years?

My manager left the company 3 years ago. I have been on good terms with him. I kept in touch with him for a few months after he left. Then other things became a priority, and I unintentionally ...
4
votes
3answers
496 views

How to handle situations which demands odd behavior [closed]

Consider the following 2 scenarios: After entering either a big shopping complex or high rated restaurant, there will be a queue and have to wait till our turn and buy/order items and then exit after ...
0
votes
2answers
373 views

How do I get a friend's attention in a polite way when they're wearing headphones? [duplicate]

Very specific question, I know, but this is something I've thought about a lot as someone who frequently wears headphones in public and has to contact people in private with them on. Often, when a ...
9
votes
3answers
1k views

How to approach a person that has stood me up several times?

Background: I met this person, S at a church I was attending at the time (I changed churches for different reasons). We became friends, because we had a few common interests, and I wanted to help S ...
-3
votes
1answer
689 views

How do I handle staying at friend's apartment in which the bathroom offers insufficient privacy? [closed]

I will be going on a business trip to the Chicago area, about 1 hour away from the city I think. My friend lives in the city and she has very kindly offered to host me for the weekend after and show ...
2
votes
4answers
2k views

Friend keeps gifting exipred items. How to politely bring it up?

Background info: the couple of times I have been in China and tried to buy some food from shops, I have noticed that all the things on sale were already past their expiry date. When discussing this ...
1
vote
1answer
747 views

How to make people understand that I am working in a part of my vast domain

I am a Telecommunications engineer who's been working as a programmer these days. One of my dreams was to continue my master degree and become a control system engineer. I always read about the ...
2
votes
3answers
1k views

How to apologize for not sending gifts to every member of the family this Christmas

My mom and I have kept in touch with my ex's parents, mostly his mom "Suzanne" and grandma. So we wanted and decided to send a Christmas card. My mom also wanted to make something for Suzanne, which ...
41
votes
10answers
18k views

How to get across to flatmates the reason behind not wanting to live with them again?

Some Background I am a 21 year old female, House mates ages: Alice is 21, Beth is 20 and Katie is 19, Obviously, the flatmates names have been changed to protect their anonymity We lived in a student ...
6
votes
3answers
2k views

How to tell my boss about his lack of hygiene

I work in a small consulting company. I love what I do and I love to work with my boss who is a kind of genius in our field. He is a quick thinker and can be very technical and smart. He is good and ...
0
votes
1answer
457 views

On a date, if I give a woman flowers, what does she do with them? [closed]

On a date, I'd like to give a woman flowers as a little present. What's the best thing for her to do with them? I mean, if I imagine to be a woman getting flowers, I'd feel real bad throwing them away ...

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