First Date After Divorce – 11 Tips For Men

A first date after divorce can be potentially nerve wracking. Men want tips, and I am here to offer the concrete advice those men are in need of. Imagine this scenario:  you are a man who married the woman you have been with since High School, have never had any other girlfriends, never dated, and now at the ripe young age of your mid to late 30’s, early 40’s, you find yourself divorced and about to go out on your first date? Here are my top 11 tips for those men who fit this situation to help you navigate this new experience.

  1. Give yourself permission to be rusty. It is okay to be rusty, don’t expect to be a smooth operator on your first date out of the gate. Even your first few dates do not expect to be a pro. Remind yourself that you are new to the dating scene and you cannot expect yourself to be a pro at something you are not a pro at.
  2. Be yourself and be honest. Do not be “fake”. Do not pretend to be someone you are not.  Be yourself. If this is your first date after being married for years, be honest about it, do not play games. For an example, if you are not ready for a serious relationship whereas the woman you are on a first date with reports she has been divorced for 5 years, been on many dates and is ready to settle down and get married, be honest that you are on your first date after being married for years and therefore not in the same place as her.
  3. Be an interested listener. The way to do that is: a) look at her in the eyes when she speaks to you and when you speak to her, b) ask her questions about herself, let her talk so she feels you care, c) reflective/involved communication: that is where you reflect back what she has said. For example, if she tells you in High School she was a cheer leader do not just say; “oh, awesome”, rather say; “You were a cheer leader? That’s awesome. What are some of your fondest memories of that time?” You see how you “reflect back” what she said by saying what she said; “cheer leader” which makes her feel like you are listening to her. Then you give her “positive feedback” by saying “awesome” it makes her feel like you give a hoot about her life and think positively about her life experience. Then when you ask her a question like; “what are your fondest memories of that time” it makes her feel like you are present in the moment with her and are interested in her thoughts. This shows involvement.
  4. Be a gentlemen! A few examples include; open the door for her, pull her chair out at the restaurant, pay for the meal even if she offers. Do not get into a fight about it if she insists on paying half because she may feel that is something she needs to do as you certainly want to hear her voice in all of this, but certainly do your best to try to make it so that you pay for it. A woman still wants to see that the man wants to pay. Another example of being a gentlemen is to state you will order several appetizers for the two of you to enjoy tasting different things. Be sure to ask her if there are any particular appetizers she enjoys to include in the selections. Be sure to let her order first, etc.
  5. Be a participant in the conversation. For example; a) share stuff on your mind too, don’t just listen, b) do your best to have a balance of where she is talking and sharing more so she feels you are interested in her, but also share some about you so she does not feel like you have nothing to say.
  6. Do not be controlling but do have opinions. Most women these days do not want to be controlled but they don’t want a wishy washy guy either, meaning, they want to know you have opinions. For example, if you both are talking about a topic, whatever it is, say for example you are discussing something that happened on the news, e.g., the presidential candidates and if she has a different opinion then you, be sure to value her opinion while giving your own. For example, think of it like this, you want to always have in mind the following; “that is such an insightful opinion. I really enjoy talking with you and sharing our opinions both when we have similar opinions as well as when we have different opinions.” No woman wants to feel like if she has a different opinion that you that you are going to force yours down her throat. Women like to be agreed with but they also value a difference of opinion if it is a healthy dialogue with the person not where they feel put down.
  7. Don’t be weird. For example, do not ask sex questions on a first date like; “do you have sex on a first date?”, or tell her she looks sexy on a first date. Rather DO tell her she looks ‘beautiful’. Not complimenting a woman on a first date is weird.  A woman wants a good compliment just don’t be weird and keep going on and on about it.
  8. All eyes on her. Do not eyeball the hot waitress or some other woman in the room, focus on her. Do not text, respond to emails, answer a cell phone call, again, focus on her and put your phone away.
  9. If there is an uncomfortable moment just acknowledge it. For example, if there is ever a long silence, no worries. You can always say – “ahhh, the long silence when two people who do not know each other are getting to know each other”, and then laugh. So, my point is, if there is an uncomfortable moment between the two of you, just acknowledge it, that usually makes the uncomfortable feeling go away.
  10. Don’t get drunk. Certainly there are many people who like to have an alcoholic beverage when out to dinner. I am not voicing a stance on whether to have one drink or zero drinks. What I am stating is do not get drunk. There is a difference between one glass of wine on a date vs. several.
  11. Just enjoy the experience. Enjoy this next phase of your life and don’t rush it! What I mean is; this date does not have to be “the one”. Just enjoy the experience of meeting a new woman and enjoy the moment and the possibility of what may be to come. Do not feel forced or rushed that you must have a serious relationship now. Try not to over-intensify it, this is your first date, just enjoy the experience.

Question: Should you make the first date romantic?

Answer: Here are 2 perspectives:

  1. Enjoy the dinner out with her and get to know her interests. The first dinner is a “get to know you” type of thing. If you like what you get to know and she likes what she gets to know then there will be another date which will lead to potential romantic opportunities and then you can plan romantic outings because this is someone you know you want to get romantic with. For example, if you know she likes to bowl, then perhaps at the next date you reserve a lane and have a rose already waiting at the lane for her when you both arrive. That is just an example to make the point that you do not have to force a romantic experience on the first date, the first date is a get to know you experience. It is that first date which will leave her wanting to get together with you again to get to know you more and want to share a romantic interlude with you.
  2. Yes, enjoy the dinner out but at a table already reserved perhaps have a rose  already set up at the table for her. That adds romance to a “just dinner experience” to open up the potential for her to see you from a romantic lens. In addition, you may consider having something planned to do after wards if the date is going well and you both wish to spend more time together after dinner. You are adults so no need to end it at dinner, make it memorable by planning something for after dinner. It is the fact that you planned it which may be considered romantic in and of itself by women. Thoughtful and romantic at times are synonymous in a first date experience. Let us take the bowling example again in this context. For the first date where dinner is the planned activity, have the bowling lane already reserved so you don’t have to wait when you get there. Or perhaps you research and discover an art museum is open or there is a fair/carnival in town. The point is, already have something in mind that you have researched before the date to know if it is open so it is planned and smooth to go to if the dinner date should so lead to the desire for more time together afterwards.

You see the difference between perspectives 1 and 2? One is a simple just “get to know you”, whereas number two helps her to get to know you and she also experiences a little “something – something” extra that leads her to really want to get together again because the night was more than just a “get to know you” it was special. Romantic and special often go hand in hand when it comes to a first date experience. What do you think? What would a woman prefer? You are right- #2 is ideal but again, this is your first time really dating, your first date actually right? Therefore perhaps you want to play it simple just to have a first date, get your feet wet in the shallow end and take your time. Perhaps you do not want it to be romantic. Think about that for a moment. Or perhaps you do want it to be romantic? What do you wish to experience for your first date? The answer to this question will help you determine whether #1 or #2 is your plan.

Certainly I would not wish for a first time dater to feel overwhelmed with information overload prior to your first date. Perhaps after your first date then you may decide you wish to do some research on line and even perhaps read some books on dating during your dating journey. Learning about dating combined with actual dating is a journey indeed. Try to allow yourself to enjoy this next phase of your life.

Bottom Line Advice To the men who are about to go on their first date:

Do not worry, have fun!


Provided below includes helpful reading if you wish to learn more about dating, expand your knowledge and feel more informed thus perhaps more confident.

Interesting article on-line about first dates:

There are many books out there, feel free to do your own research, here a few you may find interesting:

Finding the Woman You Want: A Therapist’s Advice for Men Looking for a Permanent Relationship  by Anne Rettenberg

What Women Wish You Knew about Dating: A Single Guy’s Guide to Romantic Relationships by Stephen Simpson

Changing Your Game: A Man’s Guide to Success with Women by Christie Hartman

The Nervous Guys Guide To Confidence With Women, Work & Life (Instant Infatuation) by Tristen Royal




4 thoughts on “First Date After Divorce – 11 Tips For Men”

  1. “All eyes on her. Do not eyeball the hot waitress or some other woman in the room, focus on her. Do not text, respond to emails, answer a cell phone call, again, focus on her and put your phone away.”

    Well, if she’s not looking up from HER phone it doesn’t really matter what you’re doing I suppose! It’s not men who can’t put their phones down these days…

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