5 Questions You Should NEVER Ask on a First Date

Posted by in dating after divorce, first date success, single women over 40 | 0 comments

Getting to know a guy on the first date can be a lot of fun. I’ve written posts with tips about what to talk about just in case you have trouble starting a conversation. Today’s post deals with what NOT to say on a first date. That’s just as important as what TO say. Have you ever been on a date where you or your date said or did something that was a bit of a shocker? I have heard so many WRONG things come out of people’s mouths on a first date, and I’m here to set the record straight about what NOT to say. Let’s put an end to dating foot-in-mouth disorder!

1. Are you looking to get married any time soon? Okay, it may not come out sounding exactly like that, but if you are dating for marriage, it’s best to convey that in a more subtle way. Don’t approach every date as an audition for your husband, even if that is your end goal. Imagine going on a job interview and asking the employer if you’ll be getting a large bonus at the end of the year. A bonus would be great, but this is not the appropriate time to ask for one. When you’re on that first date, first see if you’re interested in deepening the connection. If there is common interest, then you can slowly develop a relationship that might lead to marriage. Your actions and words will let him know that you are a serious dater. You can talk about all of this with greater clarity as you get to know each other. But NOT on a first date!

2. What are you into — sexually speaking? I have had clients who were asked that question ~ even before a first date, over the phone! If you’re in a sexual relationship, I believe it’s best to experience first-hand, not ask everything up front. You’ll know pretty quickly what your partner is like sexually when you are intimate with him. If you see that you’re not quite in sync, that would be a good time to gently discuss sexual matters. But NOT when you’ve just met and don’t even know each other. Bad timing….

3. Why did you break up with your last girlfriend/wife? While it’s important to know the relationship patterns of the person you’re dating, such as whether they are capable of long-term relationships, whether they cheated on their ex, and whether they were the ones who were left by their exes or vice versa, it’s good not to dwell on breakups on a first date. This can lead to bitter, angry conversations, especially if the breakup is fresh. You’re just getting to know each other. Be present with each other. Find out who he is now, with you, on this date. If you get more seriously involved, there will be plenty of time to discuss past relationships. But I would caution you to not get too engrossed in the past. Who he was with her is not necessarily who he’ll be with you.

4. How much money do you make? It’s not cool to talk about money on a first date. Or a second date. It’s more important to know a person’s relationship to money than to find out the size of his income or his 401K. I would pay attention to how generous he is. How does he talk about his possessions? Does he define himself by the labels he wears, the fancy sports car he drives? Does he seem to spend recklessly? Is he frugal? Pay attention. Those things matter more than the dollar amount he earns.

5. How old are you? If you’re dating online and your date is honest, you’ll already be privy to how old he is. Does it really matter? I think a person’s age is determined by their life experiences, how youthful they are internally and externally, how they’ve cared for themselves spiritually, mentally, physically. Age is just a number. Compatibility is determined by factors beyond that number. I have dated men who were ten years younger and ten years older than myself. Some of the older men appeared to be much more youthful and spirited than the younger men. Pay less attention to the numbers and more attention to what your gut is telling you.

Do you have any tips to share? Please share them below and happy dating!




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