I’ve noticed there are at least five uncomfortable dating conversations that people regularly contend with. These are topics that singles complain about and discuss with people other than their dates! Ideally, these topics need to be confronted and explored – or sometimes they can end up breaking up a perfectly good relationship because of miscommunication that can lead to a lack of trust. It can also be a deal-breaker in terms of both partners wanting two different things. Read on to find out why!

1. SEX

Sex means different things to different people, so we cannot assume it means the same thing to our date as it does to us. Sex can be recreational and uncommitted; it can also signify exclusivity, love or a lasting commitment. This all depends on the person and their context. So if you have important relationship expectations that accompany sex, it is best to discuss your feelings with your date early one! This way you will not be mad at your date if you find out later on that they don’t share the same notions as you do. You may be scared to rock the boat early on, but isn’t it better to know the facts and then decide?


The fact is, there are people out there with STDs. These people likely feel obligated to tell the person they are dating about their health status, but do not want to do it too soon and chase the person away. Likewise, they do not want to have sex till they’ve had that conversation and worry that their date will only wait so long. This is an uncomfortable conversation to have, but if you wait a few months to get to know each other (and become intimate), hopefully your date will be willing to consider your explanation and can then ask questions to decide how you two can best proceed. Getting it over with will be a load off for you (if it goes well), and you will be proud of yourself to know you have a relationship based on trust. Also, you may want your date to get tested before you sleep together, and this also requires a difficult conversation.


At a certain point in your relationship (often between six months and one year), one partner may want to talk about the future and maybe even marriage. Women are often afraid to bring this up as they think they will scare the guy off, but it eats away at them as they worry they are investing and wasting time in a relationship where both people want different things. You do need to give the relationship a reasonable amount of time to evolve and unfold, but there is nothing wrong with expressing your desires and finding out how your partner feels. The truth will come out eventually so you will need to take a deep breath at some point and have the conversation.


If having kids is something you know you want to do in your life, then you need a partner who wants that too. You can often see a person’s feelings on this subject just by checking their online dating profile, but sometimes it is still necessary to clarify this and discuss the your partner’s timeline for kids (particularly if you are 40-year-old woman). You may not want to wait six years and that may be his plan. So eventually it is important to explore this issue.


Sometimes daters enjoy sharing about their religion, but it can be a tense topic when they sense that different religious affiliations and backgrounds could be unacceptable to the family of origin or would cause tension in the raising of children. Eventually this needs to be discussed. Luckily, being on JDate should make this a mute issue, but you can still discuss gradations of religiosity and religious expectations. He may want to be kosher and orthodox and you are very reform.  Everything could be fine in your relationship, but if you cannot compromise on this issue, it could be the deal-breaker.

I know that you’re wishing you could keep things passionate and light while avoiding any hard conversations until you’re married. However, life and marriage are full of these tough questions! You may spend the rest of your life with someone and never have learned to be honest, to reveal yourself, to discuss challenges, or to really listen and compromise. These are very important relationship skills and, even if you successfully avoid these, other challenges will catch up to you. So, you might as well learn to be an effective communicator from the start and see if your partner is willing to do what it takes to work through things with you!

Dr. Paulette Kouffman Sherman is a psychologist and the author of “Dating from the Inside Out” and “When Mars Women Date.” She also works as a love coach and runs groups on dating and relationship issues in Manhattan. Learn more at: www.whenmarswomendate.com.
  1. Nononsense article and advise.
    Questions 4 and 5 are already in people profiles.
    Question 3. Commitment, well that depends on the person you’re with. In other words you might not be looking for a commitment, but as soon as you meet your date face to face you realize you want to spend the rest of your life with them.

    Questions 1 & 2, no one is asking those questions, at least no sane man, we all know the topic of sex is a no no on a first date… at least not before the first pitcher of Tequilla.

  2. Sorry to be so critical, but this article just cries out for negative comment.
    I can’t even begin to judge the quality of the advise itself, for that you can read Tom’s remarks, above. It is the quality of the writing; the grammar, the syntax, the very ommission of words,that renders any information useless. How could one respect the advise of a professional, an author who is so poor at expressing herself and doesn’t even respect her own work enough to have it proofread or edited?
    I gave up completely at line 3 of paragraph 5 wherein we are advised that on JDate the subject of religion shoud be a MUTE issue!!
    Perhaps it is the article that should be “mute.”
    Again, I apologize if anything I said was inappropriate or inaccurate. I am not a professional, nor an expert. I am just an average reader who would like to see the quality of the internet, in general and dating sites, in particular elevated.

  3. Fairly hypocritical, Adel, for a person to criticize the writing skills of another while misspelling the word “advice” several times.

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