Date Conversation 101: The Good, Bad and the Ugly

Submitted by SharpMan Editorial Team on Friday 8th October 2010
In this article
  • Good topics of conversation on a date.
  • Avoiding pitfalls in so-so topics.
  • Dating conversations from hell.

Couldn’t get a second date with that lovely SharpWoman and aren’t sure why? Maybe you inadvertently brought up a subject of conversation that turned her off. It’s easy to do, even for the most romantically experienced SharpMen.

Many common date conversation mistakes are made simply because (a) certain subjects are brought up too early in the relationship, or (b) they shouldn’t be brought up at all. Check out the SharpDating analysis to ensure that your next date conversation gets you the girl:

Dates as Job Interviews

Think about the first few dates with a SharpWoman as if they are job interviews, because in a way, they are. You’re basically interviewing to get a second date with her, and hopefully a third, fourth and so on. You may be having a good time and enjoying her company, but don’t let yourself get too relaxed and say something that’ll blow it.

Remember: just like you’re checking her out to see if she’s your type, she’s looking for clues about whether or not you’ll fit the bill. Everything you say and do will be examined, especially in the beginning.

As in job interviews, you should never lie, but you do want to present yourself at your best. Talk up your strengths. Minimize your weaknesses. If you were interviewing for a job, you wouldn’t want to say anything that might inadvertently prevent you from getting it, such as showing lack of ambition, negative attitude, jumping too quickly from job to job, having values incompatible with the firm, etc.

Good Topics

The SharpWomen we polled listed the following as good topics of conversation on a date. They’re safe and non-controversial, yet can be elaborated upon enough to maintain her interest and demonstrate your sharpness:

Common interests. Try to find a like interest and talk about it. Nearly any subject is game: movies, pets, athletic activities, travel, friends, etc. As a general rule, try to avoid making negative comments about your common interest — remember, this is your foot in the door.


Easy: aside from providing something to talk about, discussing a common interest lets your date know that a second, third and fourth date with you will eventually allow her to enjoy her hobby with a buddy. This is an attractive prospect to most people, so play it up.

Your hobbies or hers. A date is an opportunity to get to know the person you’re taking out. Asking about your date’s hobbies is a great way to clue in to her "non-date" personality — what she’s really like. Plus, because most people enjoy talking about themselves, you’ll get extra points just for asking and listening.

As for sharing your own, almost any hobby makes for acceptable conversation, assuming your interest isn’t an activity that could get you arrested or is considered mentally or physically destructive.

One exception: if you happen to have a "rugged" hobby like skydiving, mountain biking, or white water rafting — even better. Women seem to respond positively to hobbies that demonstrate "bravery" — perhaps this related that old caveman-protector thing?

Alternatively, don’t be too honest. For example, don’t tell her that your favorite hobby is sitting on your rear watching A-Team re-runs, even if it is. Mr. T pities the fool who can’t think of something a little more active and outgoing to talk about.

Why go to all this trouble regarding how you describe your hobbies? Again, think of a date as a job interview. When you describe your hobby to a woman, you’re enticing her with stories about what "hiring" you for future dates could include. For example, if you enjoy wine tasting, she might imagine that dating you will include trips to the wine country. If this is appealing to her, suddenly you become that much more appealing to her. Starting to get it?

The thing is, with any of these hobbies, you’ve got to be reasonably honest. Don’t say you’ve scaled Mt. Everest if you can’t even climb a fence. She won’t be impressed when she learns you’re actually scared of heights. Plus, this little fib may turn out to be a deal-killer.

Her. Just as asking about her hobbies gets you points, making an effort to consistently ask about other aspects of her life makes you look like a great date conversationalist. Ask about her work, her home, her friends; then flatter her taste, her choices, her accomplishments. Remember, as much as people enjoy talking about themselves, they love being positively enforced that much more — even from strangers!

How do you make this work for you?

The key is to ask your date a few questions about herself and then keep her talking by asking a series of follow-up questions. Then, when she sheepishly admits a success, take a moment to say "wow, that’s really great!" It may sounds simplistic and false, but you’ll be surprised by the positive response you’ll receive.

For example, if your date works as a professor, ask her about her students and lessons, then follow up with additional questions based on the answers she gives you. Similarly, you can apply this strategy to conversations about her hobbies, her family, her friends, even her pets…anything to keep her talking about herself.

Try it once and you’ll be a believer.

Anything positive. Positive people are attractive. The more positive you appear, the more likely it is that your date will enjoy herself and want to be around you in the future. For this reason, any positive topics of conversation work well on early dates. Lighthearted stories about people you know, entertaining events you’ve attended, even movies or books you’ve enjoyed, all make for good date conversation. Conversely, due to the short time span of most dates, negative topics — or even negative, self-effacing humor — may give your date the impression that you are a negative (read: not fun) person.

So-So Topics

The following topics of conversation fall into the "so-so" section because of their potential for getting too serious — or worse — boring. Why should you avoid bringing up serious topics of conversation on early dates? Because serious topics aren’t "fun" and early courtship should be. Think about it: your first few dates with a woman are more about amusement and escapism then about hard-core reality. Who wants to go out a stranger who’s gonna bring you down, right? Bringing up serious topics is more likely to turn your date conversation in the wrong direction. For example:

Your career. It’s one thing to get her to talk about her career, but quite another to go on and on about yours. If she asks about what you do, describe your current position, your responsibilities and where you see your career going. Be positive, light-hearted and confident, but don’t brag. Never share work frustrations during an early date. Once you’ve covered the basics, segue out of this topic of conversation with a related question about her or a short joke. That’s it. Why? Because early dates must be kept light and entertaining, and there’s a good chance that talking about your work won’t be.

Current events. Theoretically, current events present no inherent date conversation danger. After all, it’s always positive when your date demonstrates that she keeps up with what’s going on with the world. Unfortunately, stories tend to become news become they push people’s buttons. Every news event is underscored by strong moral, political and religious opinions — all polite dinner conversation no-nos. Why? Because people generally disagree on these issues and can take strong offence when presented with another opinion. For this reason we suggest playing it safe by avoiding long discussions about current events — just in case.

Your relationship with your family (as long as it’s positive). You may discuss your parents’ names and occupations; number of brothers and sisters, and their occupations, spouses, and children; where they all live; and their pleasant attributes. Amusing stories about growing up are fun and show that you have a healthy attitude. However, be careful not to go overboard and give the impression of being a "mama’s boy" — an adult who’s too close to his family can be a turn-off to a woman.

Of course, if you don’t have the greatest relationship with your family, it’s best glossed over. Early dates are not the time to let her in on your family problems — again, it’s a turn-off. If your family can’t seem to get along and she brings the subject up, consider smiling and saying something like, "I love my family, even if we don’t always get along. You know how it is!" Since most people do know how it is, she’s likely to smile back and allow you to subtly change the subject. As you get to know her better you can be more forthright about any family squabbles.

Bad Topics

Despite the fact that many seem obvious, bad date conversation topics are brought up by SharpMen every day. Why the flubs? Often a bad topic is brought up because a SharpMan begins feeling comfortable too quickly, gets nervous, or is trying too hard to impress. We suggest avoiding the following at all costs:

How much money you make. Some successful SharpMen — particularly those who feel that they were less-than-suave in high school — are under the mistaken impression that talking or "hinting" about a fat paycheck will make them look more attractive to their dates. Bad move. Apart from being tacky, bragging about your wallet makes you look insecure — and insecurity is unattractive.

But, isn’t a financially successful mate something many SharpWomen look for? Well, in many cases yes, but there’s nothing sexier than a successful SharpMan who’s humble about it. A guy who has to blab about what he’s got screams, "Apart from not having any inherently attractive qualities, I am also not confident. For this reason I have to bait women with my wallet!" In other words, the old "luxury sports car = small Johnson" theory.

Talking about your wallet can also be insulting to your date. It presumes that her romance equation necessarily includes money, along with chemistry and compatibility — which, even if true, is not something she wants to you to acknowledge.

Bottom line? Your date should be there to get to know you. Bringing up your bank account when she hardly knows you is a great way to attract unscrupulous users and turn off women of substance.

Personal problems. While everyone’s got some baggage, early dates are not the time to share it. Would you enjoy a first date with a woman who talked incessantly about her past fears of commitment, her bitter custody battle, or the unhappy childhood she’s still working out in therapy? For most men, this woman would be quickly classified as a self-absorbed "project" better left to the "fall back" category.

Many guys bring up similar topics, thinking they’re being open and honest. While it is important that your SharpWoman get to know the "real" you, this level of disclosure is too overwhelming for early dates. Learning so much about your "problems" so quickly may prevent your date from focusing on your good points, and will likely make her feel uncomfortable — not the first date impression you want to make, right?

Jokes about painful subjects. On the other hand, if your date shares a personal detail about her life — the death of a pet, the loss of a job, a serious illness — don’t let the discomfort associated with hearing this personal information make you look like a jerk. Avoid cracking a joke or offering advice to fill the silence. Simple say "I’m sorry, that’s terrible." Then let her change the subject. This way you’ve been supportive, but not nosy — and you haven’t inadvertently said something to make your date burst into tears at the table. Bonus.

Bodily functions. For some unexplained reason, the pure joy of a successful bowel movement and the hilarity of passing gas may be lost on your date. Save this discussion for the locker room. Enough said.

Former relationships and bad breakups. Many people have a "put it all on the table" attitude about dating. We disagree. Early courtship requires a bit of "dancing" and mystery. For this reason some things are better left in the past. Consider keeping your past relationships, lovers, breakups and erotic escapades to yourself — for the early dates or forever. If you’re divorced or otherwise split from a long-term relationship, it’s natural to mention your status in passing, but it’s not necessary to go into great detail about the problems that caused your relationship to end.

Discussing your bitterness toward an ex or how you were "victimized" — no matter how bad your breakup — also demonstrates to your date that you are not ready to move on to a new relationship. Strike one. Additionally, no one enjoys the company of a person who sits around feeling sorry for himself and speaking negatively about others — even if it’s deserved. Strike two. If you must, share the details of your past relationships later on, but skip them on early dates.

Beautiful women. Don’t talk about how hot Julia Roberts is in her latest movie or how your waitress looks just like last month’s centerfold. Keep your eyes to yourself — or on your date. Try to give your date your complete attention. Ideally, she should feel — at least while you’re out together — that other women are invisible to you. Believe us — women find this irresistible.

Controversial religious and political topics. Many SharpMen feel strongly about these subjects and would like to know where their dates stand on these issues. Unfortunately, a simple statement of opinion can escalate into heated debates or arguments. We suggest avoiding these subjects like the plague. An argument pretty much guarantees there will not be another date.

And what about those issues that you feel you need to know her opinions on in order to determine whether you’d like to see her again? If compatible beliefs are a prerequisite for any of your companions, we suggest asking subtle, non-inflammatory questions in order to learn how she feels in a polite, SharpMan-like manner.

This article last updated on Friday 8th October 2010
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