Personal — Conversation Starters

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.

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.