EBR 043: How To Handle The First Date With Your Ex Boyfriend

It’s funny…

I am currently in the process of writing a massive guide about going on dates with an ex boyfriend when I stumbled across this question from a woman who wants to remain anonymous.

Now, there were a few things that drew me to her question.

Thing #1: I am trying to make a conscious effort to delve deeper into face to face interactions with ex boyfriends since I think that’s a major weakness of this website

Thing #2: My wife and I both agree she has an AWESOME voice!

Thing #3: She asked a question that I thought was really interesting.

What’s the question?

“Should I ask him to hang out with me?”

Perhaps I should give you some background.

Anonymous and her boyfriend have been broken up for a few months and she has done a phenomenal job of sticking to my advice. Specifically the no contact rule.

Here’s the thing though.

Her ex boyfriend is currently in possession of a record that she wants back and her ex actually called her to set up a day where they can meet up and he can give it back. Thus, she is wondering how to turn a meet up that’s supposed to be about a record into a date where they can hang out.

That’s just one of the many questions I answer in this podcast episode but first lets do a quick run down of anonymous’ situation,

Her Situation

  • She dated her ex for 2 years
  • The breakup is classified as “mutual”
  • She did the no contact rule and feels it was a success
  • She has a record that she wants back
  • They set up a date to exchange the record
  • She wonders if she should ask him to hang out

Important Links Mentioned In This Episode

Podcast Transcript


Welcome to the ex boyfriend recovery podcast where we help you get your ex back and have the fairy tale ending you deserve. And now, you’re host, he’s been dubbed as The Ex Whisperer, Chris Seiter.


Hello and welcome to another episode of the ex boyfriend recovery podcast. I kind of took a break last week, mostly focused on Youtube and creating videos because I really–I guess it’s fun to be on camera. And there’s a lot of more interesting things going on but the podcast is still near and dear to my heart. So, here I am again for another week and another episode of the ex boyfriend recovery podcast.

As far as what’s going on with the website, not much new things going on. I am actually in the process of rewriting my most popular book- Ex Boyfriend Recovery Pro and this thing is going to be a behemoth. It’s going to be a monster. I really took a lot of the people who complained about what the book didn’t have or what the book lacked in the past. I jotted those notes down and basically everything that anyone ever complained about is going to be going in the book.

Now, you may be asking yourself, “Well, how can this book be specific to my situation?” Because without a doubt, that was the number 1 complaint. You know like, “The book created this nice little template for me to work in but it doesn’t speak directly to my situation.” I’m glad you asked that. That was actually the remedy in this new book coming up. I don’t know when it’s going to be completed because I want to do a really good job for you but basically what’s going to happens is I have compiled a huge list of all the situations I’ve ever encountered through ex boyfriend recovery.

And I am structuring the book in a certain way where it creates a game plan for you to follow and then based on your situation, it’s going to teach you how to alter that game plan to fit your needs perfectly– long distance relationships for example. So, yeah, I’m super pump about it, you know we just finished writing a new book– The No Contact Rule Book. If you haven’t seen that, check it out, I’ll link to it in the show notes. Let me kind of make a –jot it down here. So, I don’t forget but yeah, we’re really excited to add more products to fray and I have to say, thank you guys for being so accepting of the newest additions to the ex boyfriend recovery team.

We’re trying to create this family atmosphere where we help everyone, where we get and respond to everyone but enough about that. Let’s just get right down to it. Today’s question comes from someone who wanted to remain anonymous but she has a real interesting question that I don’t think I’ve ever covered on the podcast before. Well, of course until today. So, let’s hear from—let’s just call her anonymous.


Hey Chris,

It’s awesome that you do this. Thank you so much. I’ve referred to your website a lot. So, anyways– two year relationship, ended basically in the “Girl’s-a-crazy-this-guy’s-a dumb” paradox thing. Pretty mutual breakup. Pretty cut and dry. Not to Sloppy. No contact was a success for 30 days. Light texting after no contact, although he is very reserved but responding and when our last conversation went right, I asked if he has still had my old records that I lent him and he does and he agreed to meet up and give it back but yeah. So, this is kind of where I’m stuck. We’re going to be meeting up this meeting up this next week. I kind of feel like I’m setting a trap. He probably thinks I just want my thing back. So, I can leave forever but I mean, what do I do? Do I ask if we hang out for a little bit or you know, I’m definitely going to be very chill and nice and positive when I see him, not bring up any heavy memories. I get that but yeah—I need some advice.[laughs]

So, if you can get back to me, I’d really appreciate it. Thank you, so, so much for even having this advice page. You’re awesome! I look forward to hearing from you and yeah right on! Have a great day! Thank you!


You know, I have a bit of a funny story to tell. When I am choosing questions to feature on the podcast, often times my wife whose desk is sitting right next to mind, listens to me listen to all voice mails and you’re particular question, when I was playing it, listening to it, I was interested in it.
You know I was taking notes and my wife she was sitting right next to me and she stopped everything she was doing and she was listening as well which is kind of rare for her and then after you were done talking, she literally turns to me and goes, “I really like her voice. Her voice is awesome!”

So, that’s when I knew for sure that I definitely had to feature your question on the podcast but anyways, you have done a pretty good job at advancing to the point you’re at currently. Have you done a perfect job? I don’t think so. I’m not trying to say anything mean to you or put you down or anything like that but if I were to pick on something that maybe you didn’t do as well and you weren’t as descriptive as maybe you could have been but if there is one thing that I can kind of pick at that maybe you could have done a little bit better not relating to a date. It’s kind of the lead up to the date. I teach a very specific method when it comes to getting an ex boyfriend back.

I’m of the mind of the value chain where you have to start off slow and kind of slowly build up the attraction into a point where it boils over and he just can’t not be in a relationship with you. To me it looks like, you’re maybe rushing a little too fast but I’m not saying you shouldn’t go get your record or anything like that. I’m going to give you certainly tips on what to do during the date but I would say, after the date, focus on building more attraction before you see him again in person.

I’m actually writing a really good article coming up about this very kind of question that you asked, which is another reason why I picked your question because I’m literally writing an article about it and when you were asking about how to handle the date or what you do during a date, I just thought it was a perfect match for what I was already currently working on.

So, what could you do differently in leading up to the date? Let’s cover that first. You did the no contact rule which is phenomenal but where I think you fell down a little bit was the attraction building through texting and then after texting you have to transition to phone calls. You have to sort of build attraction in each of the mediums. Build attraction with your ex through text messages and then of course build attraction through your ex through phone calls and eventually, once enough attraction has been build, the date should be easiest. Just sort of, kind of, if you imagine a graph, it’s sort of like the graph is constantly going up if the graph were to represent attraction of course.

But it seems to me like you’ve already advanced to where you’ve locked down a date with your ex boyfriend. So, congratulations for that and I’m going to do everything in my power right now to help you on the date. So, when it comes to dating your ex, if I were to pick out one of the weakest parts about ex  boyfriend recovery, it’s the fact that we feature a ton of advice on the first parts of my overall strategy for getting an ex back, for parts like the no contact rule, parts like text messaging, parts like talking on the phone but we don’t really talk about dating a lot and what to do during the date. I certainly have written long in depth articles about it. Of course I write about it in my products and everything like that but for whatever reason, I’ve just never covered that as much. I think that’s partly due to my laziness but it’s also partly due to no one really wants to hear about it because where people mostly struggle is in the first parts of the strategy with the no contact rule.

I mean, I think something like 70-80% of people fail at the no contact rule. So, I think a lot of my effort or focus is on helping those people at the beginning of the strategy but that doesn’t mean we should leave out the people who are the end of the strategy– dating. So, when it comes to dating, there’s a lot of different aspects. As far as what to say, I think this podcast episode is too short to tell you exactly what to say on a date. I will give you a few pointers a little bit later but let’s talk about what kind of a template to work in because I always think people look better when they have an overall strategy.

So, when it comes to dating you shouldn’t operate under the assumption that it’s going to take one date to get your ex-boyfriend to agree to be back in a relationship with you. Never operate under that assumption. Why? Because often times, this process takes longer. Imagine that you were about to go on a blind date with someone you’ve never met before and then on the blind date, that person asks you to marry him. Would you say yes? You’ve never met this person before. This is the first time you’re ever meeting him and he’s already asking you to marry him. Seriously?  Of course you wouldn’t say yes. Of course you would say no. And that’s kind of how I look at it when women try to rush this process. This process cannot be rushed.
You cannot be asking your ex-boyfriend to marry you right off the bat. Just like you can’t asked him to be in a relationship with you right off the bat. This process will take time which is why I like to teach what I like to call the three date method. Now, if you listen to my strategies or read anything on my website, you know that I’m a big fan of slowly building up attraction and the same applies with dating. When you see your ex-boyfriend in person. You should go on three dates. The first date should be real light, not threatening, but interesting enough to hold his attention to make him think about you. The second date should take things up a notch and on the third date of course should take things up a notch and then ideally by that third date enough attraction has been built through both where he’s re-evaluating whether or not he wants you to be his girlfriend and he’ll ask you.

Now, what happens if you go on each of these three dates? You know you go on what I like to call kind of a small date, the medium date and then large date or the romantic date and he still hasn’t asked you to be his girlfriend again. Well, then I then I think you keep repeating the process. Not over from the beginning but repeat the process with the last romantic date. Repeat it to where it’s every single date you go on from this point on after that third date is romantic and puts him in the mindset of wanting to ask you to be his girlfriend again but we’re getting way ahead. Right now, for your particular situation, you are at the small date portion.

So, one of your big questions was should you ask him to hang out because you say he’s operating under the assumption that he’s just going to give you your record back and then that’s going to be it. Well, you shouldn’t ask him to hang out. You should just do it. I’m about to give you my surefire method way that it can work. Meet him at a coffee shop okay? Starbucks is perfect. Meet him during at the middle of the day, at a coffee shop, Starbucks alright? Exchange things not in the parking lot but in Starbucks.

So, here’s how you can get him to come into Starbucks and sit down next to you. You arrive an hour—maybe an hour is too much. Maybe 30 minutes early. It just depends on—I know some men out there get really keyed up and they show up a lot earlier. I was that way. Where I would have a date set up and I would show up maybe 30 minutes early because I was just nervous about it but my point here is you’re trying to go on small date and the goal of this date is to interest him and make him want another date with you. And the best way to do that right now is to go on a small date at Starbuck’s. We’re using Starbucks as an example because I’ve been to Starbucks and I’d know exactly how this can work. So, once you get there early, go inside of Starbucks and then order a coffee or whatever the heck you want to order there, Frappucino, whatever. Then sit down because they often have comfortable couches or chairs. Sit down at a Starbucks where there’s an open chair near you and then when he shows up, he will come inside Starbucks and then he will see you and then he’ll V-Line towards you and then you’re both sitting, he’ll give you your stuff and rather than asking, “Hey, let’s hang out after this.” You’ve already put him in this position where he’s going to hang out with you.
So, now that you have him in Starbucks, this is your time to shine. What do you say? Well, you just have to interest him, you’re right about being chill and not bringing up really bad memories or super emotional stuff. What I think you should do is talk about interesting stuff. Things that make him laugh. I always like to say get down to a soul. Sort of, talk about really interesting things that affects him on an emotional level. I’m trying to think. My wife and I last night, we had an interesting discussion about the bachelor of all things and how the bachelor almost glorifies cheating and how it’s socially acceptable for the bachelor or even the bachelorette to cheat and how it’s such a way of process.

Now, should you talk about that? No. Especially if there was cheating involved, you should definitely not talk about that but talk about something that’s going to interest them. A tv show is an example there that I just used but maybe he has a movie, maybe—I know Game of Thrones is coming out soon which is we’re super pumped for. Maybe he’s a huge Game of Thrones fan. Maybe you talk about that. Talk about things that you know for a fact will keep him engaged and interested. Now, here’s the important part. Who should end the date? You should. You should always end the date prematurely.

I’ve talked about this a lot throughout ex-boyfriend recovery and it’s sort of ending the conversation at the high point. Well, the same principle applies to dating. You want to end the date at the high point of the date. The point where he is enjoying the conversation so much that he doesn’t want to leave. That’s when you should leave. Because when you have him on that hook, when you have him hooked and you leave, you are putting yourself in a position where he’s going to want to see you again. And everything after that will be so much easier. You’ll find he’ll text you more, he’ll think about you more, he’ll say nice things to you, he’ll say maybe I miss you and then you can go about setting up that second date; the medium date which I’m actually not going to talk about because I want to talk a little bit about what you should wear.

Now, I am not, definitely not an aficionado when it comes to fashion. I think if– I would always let my wife dress me because that’s how bad I am at dressing up. If it was up to me, I would probably go everywhere in tennis clothes because they’re so comfortable but obviously, I can’t do that. But anyways, here’s some interesting things that I’ve learned and also that my wife can help you out because now my wife is working full time with the ex-recovery team and she’s specifically really good at things like make up and dressing things up. You know women, they just—I’m a guy. I can’t really give you much insight into that. So, I went out and got someone who knows a lot about it, enough to get me to marry her, my wife.

My wife the other day, she sent me this really interesting email and specifically, she’s in charge of Youtube and she wanted to do a Youtube video on make up and dressing up clothes and everything like that. She sent me this really interesting email about what the clothing says about you and what the color of the clothing says about you. I’m sure you’ve seen this when it comes to like sales and advertising and how like yellow—you know like McDonald’s has red-yellow or something because it catches your eye and it makes you want to go in but when it comes to relationships, it’s really interesting in what the colors mean. So, according to this, there are three types of colors that you want to wear on your first date.

The first color is probably the most recommended color and that’s red. Now, red represents passion. So, if you want him to look at you in a passionate way or you want him to be super into you, red is definitely what you want to wear. The second one is perfect if there was cheating involved, specifically if you cheating and, that’s Blue. Baby blue in particular—I know from my sales experience that Baby Blue is the most trusted color but Blue in general shows that you’re trustworthy and that you’re secure essentially. So, if you cheated or there was cheating involved, blue is definitely the color that you want to wear. And then finally, if you feel like you want to look slimmer or you feel that like Red looks terrible on you, –these are my wife’s words, I’m just summarizing from the email here I have pulled up in front of me. Yeah, some relationship expert this guy is! ? But if you think like Red isn’t like good on you or maybe you think you look a little fat in Red or maybe you want to slimmer, Black is the way to go. Wear something Black because it exudes powerfulness—powerfulness, that’s horrible. It says that you’re powerful and sleek at the same time. Now, those are the three top recommended choices for what I think you should wear on the first date.

As, for other things, Yellow equals optimism. Orange equals friendliness and confidence. Purple equals creativity. Green is peaceful and healthy—really interesting there. And then Gray and Silver equals balance and calm. So, however you want to appear on the first date here. I don’t know—I’m not even trying to call this a date. It’s sort of like a small date. You know the Starbucks thing I was talking about. Pick which one you really want to appear. My personal choice, I’d say Red—passion. Because you want him to look at you in that passionate way again but if you want to maybe be more creative, wear Purple. If you want to show optimism—wear Yellow. So, as far as what to wear, those are my recommendations. As far as what to say, like I said, get down to a soul. Talk about something that you know will interest him and then end the date prematurely on purpose. You always should be the one to end the date prematurely.

So, those are my top tips for what to do on a first date-small date. Remember, do not ask him to hang out. Just put him in a position where he’s forced to hang out with you, as simple as that. Don’t ask permission. Just put yourself in the position where he’s forced to hang out with you. Trust me that will work.

I think that’s going to do it for today’s episode. If you haven’t already visited ex boyfriend recovery, please do so, www.exboyfriendrecovery.com . I want to ask you to please subscribe to this podcast if you like what you hear. Every single week I post a new podcast episode. So, I’m committed to it. You will always get really good and insightful information from my podcast specifically about ex’s or just relationships in general and also please if you haven’t, write a review. Even if it’s a bad one. I encourage you to write a review on Itunes for my podcast and that it’s going to do it for this week’s podcast of the exboyfriend recovery podcast episode. Man, I just totally messed that up. And that’s where I’m ending it today.


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6 thoughts on “EBR 043: How To Handle The First Date With Your Ex Boyfriend

  1. EBR Team Member: Amor

    Hi Maia,

    I just want to make it clear, your videos together are what makes him upset most of the time?

  2. EBR Team Member: Amor

    Hi Michelle,

    that means you have to pick a more romantic or engaging activity for the next dates, the second date should be more activity oriented, a little longer than the first date.. Like doing rock climbing.. and then just spend half a day or less with it.. talk while eating after it and then end it

  3. Maia

    Hi Chris & Amor,

    I’m wondering if you can help me as I’m not sure how I should help my ex, or if I should just distance myself from him.
    We’ve been texting for 2 weeks every day now since NC ended. At first he was happy to hear from me. But for the past week or so every single message has been about him complaining about his life, how stressed he is, and not really responding to my attempts to try and cheer him up.
    He’s also now starting to leave it days between each reply, hiding his last online status and generally not talking in a positive manner about anything. He has agreed to meet up for a coffee in a week or so, but nothing concrete has been organized yet.
    He’s an introverted guy but I don’t have the time to chase after him with my work being so hectic atm. I also don’t want to cause more drama and make a repeat of our last relationship together where I made the mistake of chasing him.
    I’m finding it hard because no matter what I say he seems determined to be negative. He’s mentioning randomly in our conversations that by watching videos of us together he’s upset, we were so happy then etc. I try to reassure him but it doesn’t seem to work :/
    It’s now been 4 days since my reply to his last message. Should I back off and give him time to deal with things? Or is there anything that I can do to help him feel more positive?


  4. Michelle


    I am past NC and past the first “small” date with my ex. I followed all your advice and so far it worked like a charm!

    However he wants to see me again, this is great news and helping me feel super confident. Could you please describe what the medium (2nd) and large date (3rd) look like?

    I loved how to described how to go in and buy the coffee sit down before he got to the coffee shop. I am literally so lost when I think about the medium date. I am afraid if I don’t have a general outline of how to act and what to do then I will mess up the progress I have made.

    Any advice for me?

    Thank you,


  5. Chris Seiter


    Love it haha.

    I suppose you would have to alter the value chain. How do you usually communicate?

    By phone?

  6. Purple Rain

    I heard this episode and was wondering how you would work up the value chain if your ex does not like texting to begin with?


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