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Conversation Starters for Friends You Haven’t Seen In a Long Time

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Has this ever happened to you? You’re in the subway station, waiting for a train, and you run into an old friend from high school whom you haven’t seen for about 4 years.

Unless you’ve recently moved on the other side of the planet, chances are something like this happens to you every once in a while.

The Old Friends Paradox

I find that many people struggle to start a conversation with an old friend they haven’t seen for a while. They may have been really close once but as the time passed, the emotional connection faded, and the common ground between them narrowed.

You have different lives now; you’re not used with seeing each other anymore. This can create an awkward feeling and a lack of momentum when meeting an old friend, either intentionally or by accident.

Conversation Starters for Old Friends

In such contexts, there are always good conversation starters you can rely on to get the conversation going. Here are some of the most valuable conversation starters for friends you haven’t seen in a long time:

1. How have you been? What have you done? Conversations with old friends are a good opportunity to catch up on things. Since a lot of time has passed since you’ve last seen each other, use conversation starters in the form of questions about what happened in the friends’ life during this time.

2. Job and family. If you want to use more specific questions to find out about your old friend’s life, there are two evergreen areas which you can explore: the job and the family. Consider question such as: “Where do you work?”, “What do you do?”, “What’s that like?”, “Are you in a relationships?”, “Do you have kids?” etc.

3. The good old days. I’m not a big fan of dwelling on the past, but every once in a while, it’s good to remember the fun shared experiences from the past with an old friend from that past. It brings that sense of bonding back. So, use convo starters in the form of “Do you remember when…?”

4. The common acquaintances. I am also not a big fan of talking about other people’s lives. However, meeting an old friend can be a good opportunity to find out about other friends or acquaintances you both know which you’ve lost touch with. Just make sure you ask about the lives of people you actually give a damn about.

5. Remember old dreams. On out of the box way to initiate a conversation with an old friend is to ask them about the dreams you know they had in the old days and what’s going on with them right now. For example: “I know you wanted to have you own business in high school. How’s that going?”

Such questions can be tricky because you may dig up a bad memory of an abandoned dream, but they can also be a chance to find out some good news and build some connection. I think it’s definitely worth trying this approach.

I know many cases when old friendships got brought to live again by one interaction after a long time and both parts were very excited about this. If this doesn’t happen, at least you still get a positive, enjoyable conversation.

How to Deliver a Conversation Starter with Style

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You’ve probably heard it said before that it’s not what you say; it’s how you say it. Well, when it comes to starting a conversation, it applies more than ever. This doesn’t mean what you say doesn’t matter. However, it is mostly how you say it that communicates your attitude.

There is some famous research done by psychologist Albert Mehrabian which points out that our emotions and attitudes are communicated only 7% through words, 38% through the qualities of your voice, and an amazing 55% though your body language.

I believe that the best attitude that you can communicate when delivering a conversation starter is being relaxed, friendly and confident. People will tend to respond a lot better to other people with this attitude, no matter what conversation starters they use.

There are 5 ideas I think are important to apply when delivering a conversation starter, in order to get the best reactions possible:

1. Speak fluently. You don’t want to stutter or stumble over your own words when delivering conversation starters. Make sure that once you chose a conversation starter, you don’t switch to another one in your head, fearing you didn’t pick the proper one. What’s done is done: once you chose what to say, say it in clear, straightforward way.

2. Speak slowly and loud. It often happens for a person to be somewhat nervous when initiating a conversation. It sometimes happens for a person to be shy. Both these things tend to make one speak fast and in a low voice. If this is the case for you, consciously do the opposite instead: use a medium to slow speaking speed and a medium to high speaking volume.

3. Orient yourself towards the other person. When you start a conversation, you want the other person to know you intend to have a conversation with them and to get them committed in it. You do this by orienting your body and your head towards the person you’re talking with, maybe at a slight angle. I know there is also this popular idea of talking over your shoulder when initiating a conversation, but I’m not a fan of it.

4. Keep eye contact. Looking at the person you’re talking with is a basic sign of respect and confidence. It also keeps the other person interested in listening to you and talking with you. There is no need to stare at the other person, but do keep eye contact with them about 2/3 of the time when kicking off a conversation.

5. Shut up. After you use a conversation starter to initiate a conversation, you want to let the other person take it from there: answer your question, make a comment, whatever. You don’t want to go: “What do you think about this party?… I mean, do you like it? Is it like you expected?… I love it! It’s the coolest party I’ve been to lately…”

Use your conversation starter, then shut up. Even if the other person is slow to pick up the conversation, have patience and give them some time. Remember it’s a dialog, not a monologue.

Delivering a convo starter with style is a reflection of your people skills and your confidence level. You can improve how you deliver conversation starters by working directly on your body language and voice, but keep in mind that if you want to go to the next level, you’ll need to work on your people skills and confidence as a whole.

Conversation Starters for a Company Party

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Especially in certain periods of the year, company parties are everywhere: your company, clients’ companies, suppliers’ companies etc. Many people find company parties boring and only attend them if the feel obligated to do so.

It doesn’t have to be this way. A company party can be a great opportunity to meet new people and strengthen relationships with people you appreciate, to network and have fun at the same time; particularly if you know some good conversation starters.

The Professional-Personal Mix

People often feel confused about starting and having conversations at a company party because they don’t know if it’s best to treat them in a more personal or a more business way in terms of topics.

Considering it’s the party of a company, starting a conversation talking about business related topics is perfectly OK: the job, the latest business projects and the company.

On the other hand, keep in mind that it is a party after all and people attending it often like to forget about business for a while. For this reason, it’s best not to talk about professional stuff the whole time and eventually transition to personal topics. It is also fine to use convo starters that take the conversation directly to personal topics.

Conversation Starters Ideas

Let’s take things one step further with some smart ideas for conversation starters which you can use at company parties:

1. “How’s work going for you?” – A simple, straightforward, work related conversation starter which work great, unless the other person is very shy or hates their work.

2. Ask about specific projects – If you want a more specific approach, use more specific questions such as “What projects have you been working on lately?” or “How is project X going?”

3. Give a compliment – It can be about the person’s choice of clothes for the party, their recent promotion, their success in a challenging project, anything you can honestly compliment.

4. Make a comment about company parties – Every person who has attended at least a couple of them has some thoughts about them. Don’t be afraid to admit you find most company parties boring but you hope this one will be fun. This can be a good way to build some rapport.

5. Latch on the time of the year – Most company parties are near Easter, Christmas, or New Year’s Eve. So, ask questions about preparations and celebration of that particular event.

6. “How are things outside work going for you?” – Get personal and get to know the other person with their life outside of work.

7. “Married? / Kids? / Plans in this area?” – If you like to talk about family, do use this kind of conversation starters. Many people enjoy talking about their family; it’s a very warm topic.

8. “Do you believe the people who are promoted in a / this company are the people who fit in?” – I love to start conversations using business related opinion openers. Just make sure you’re actually interested in the opinion you’re asking for.

These are just some ideas. I’m sure you can find many more good conversation starters for a company party as long as you understand the basic principle. Good luck with them and remember to enjoy the ride!

Funny Conversation Starters

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I believe one of the most important qualities that good conversations have is that they’re fun. They pull you in through their joyful and positive aura. If you’re gonna have a fun conversation, you might as well start it in a funny way.

Not all conversations are proper to be initiated using funny conversation starters or any funny conversation starter; this does require calibration. Nevertheless, I find that people in general are much more hesitant to use funny conversation starters than it’s warranted.

The point is not to force yourself to be funny, but to permit yourself to be funny. This applies especially in the beginning of a conversation, when it’s less probable for this to happen.

20 Funny Conversation Starters

To help you kick off conversations in a humorous way, here are 20 funny conversation starters. For this round, I’ll only stick to question-type convo starters:

“How did you find out there is no Santa? You did find out, didn’t you?” (I often ask this; I really wanna know!)

1. “What do you think about laissez faire capitalism?”

2. “Do you know any good conversation starters?”

3. “What do you wanna be when you grow up? (Use it with adults)

4. “Are you a good girl/ nice guy or a bad girl/ bad boy?”

5. “What do you think about raising ostriches?”

6. “Do you have any food with you? I’m hungry!”

7. “Heard any good jokes lately?”

8. “Do you think good girls go to Heaven?”

9. “What do you think you were in a past life?”

10. “What was the last stupid thing you did?”

11. “What do you have a weak spot for?”

12. “What’s your opinion about black nails on men?”

13. “What did you wanna be when you were 5?”

14. “What’s your favorite color?”

15. “What’s the yuckiest food you ever tasted?

16. “What do you do when you’re home alone and the power goes out?” (I love this one!)

17. “If you could, what superhero would you want to be?”

18. “Read any scandalous news lately?”

19. “What’s the best present you’ve ever received?”

20. “Do you think they’ll make another Batman movie?”

In my view, initiating conversations in a funny, relaxed way is one of the most interesting people skills you can master. A conversation started with a laugh is a conversation with a lot of potential. Keep this in mind as encouragement to yourself to employ funny conversation starters.

First Date Conversation Starters

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Have you noticed how first dates make most people somewhat nervous? Have you noticed how we sometimes find it difficult to kick off a conversation on a date? This is where first date conversation starters can be of good use.

First Date Conversation Guidelines

Here are, from my perspective, the general rules for using first date conversation starters:

  • It is OK to start the conversation at a personal level, ask the other person about themselves and talk about yourself. After all, the point of a first date is to get to know each other. It is also not obligatory to start at a personal level.
  • It is best to start the conversation light. Don’t be afraid to ask personal questions, but don’t ask the other person about their mission in life right off the bat either.
  • Try not to make your first date conversation starters sound contrived and weird. A normal, relaxed start to a first date is the best start.

10 Good First Date Conversation Starters

Besides applying these guidelines, what can further help you is knowing a few good conversation starters from which you can choose. Here are 10 of them:

Comment on the clothes and accessories. Your date probably took a lot of time to dress and get ready for the date; you might as well be romantic and reward that. Take a moment to notice their clothes and accessories, and make an honest compliment on something you like.

Comment on the date location. The place where you’re having the date is another good conversation starter. Consider questions like: “Have you ever been here before?” or “What do you think of this place?”

Review the day so far. One of my favorite first date conversation starters is asking: “How was your day?” This works great since most dates take place in the evening. Also, be ready to share some of your day.

Ask them about a fun thing they did recently. Fun conversations best start by talking about fun things. Get the other person to think and talk about something fun they did recently, and I bet it will put a smile on both your faces.

Pick up the thread of a previous conversation. If this is your first date but not the first time you’ve talked, a great way to start the conversation is to remember the subject of an interesting conversation you had last time and pick it up from there.

Pick up on something you know about the person. An alternative similar to the one above is to think of something you already know about your date which seems interesting and start from there: “So, you’re a marine biologist. What’s that like?”

Ask them where they usually go out. Talking about favorite clubs, bars, restaurants, coffee shops and places to hang out is often a good conversation starter; especially if you are both active and sociable people.

Ask them what they do in their free time. Hobbies and free time activities are another alternative for a first date conversation starter. There is usually a lot to talk about on these subjects, even if you’re both kind of workaholics.

Ask them what they do for a living. Speaking of workaholics, convo starters related to current jobs never get old. If you already know what the other person does for a living, consider asking for specific details about that job.

Ask them about themselves. This question is a particularly good start to a romantic first date. It opens up the conversation and it creates so many conversation possibilities on a first date that I sometimes wonder why there isn’t a law which makes it mandatory.

Last but not least, keep in mind that first dates are meant to be fun, exciting and intimate moments. If you’re spending too much time thinking about first date conversation starters and stressing to discover the perfect one, you’re missing out on a great experience.