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Book Excerpts From 251+ Dating & Relationship Regrets by Bart Smith

Get a sneak peek into 251+ Dating & Relationship Regrets by Bart Smith by reading a few of the hand-picked book excerpts below. If you like what you read here, then you'll definitely love the book or perhaps the audio version. That said, enjoy these excerpts!


Relationship Regrets (Introduction & Welcome Message)

They say, if you don’t learnnnn from the mistakes of your past (or the experiences of others), you’re doomed to experience them yourself sooner or later or even repeat them. No one wants to regret anything especially in the areas of dating, having sex, and/or getting married. Right? Those regrets can ...


Top 21 Relationship Regrets Men & Women Have With Dating, Sex & Marriage

(#1) Not taking things slower and rushing into having sex, moving in together, getting married to soon, etc. (#2) I regret having sex with him/her, and not insisting we make this more than just hooking up. I had feelings for ...


Dating/Relationship Regrets #52-72 You Too Should Avoid ...

(#52) “I regret leaving the relationship on bad terms and saying the things I did. Our last moments together were filled with yelling, screaming, name calling, throwing things and well ... it didn’t end well. I could have been ...


Dating/Relationship Regrets #152-182 You Too Should Avoid

(#141) “I forgot, what follows friends with benefits -- a potential serial cheater? Even open relationships are risky when you‘re both playing musical beds. Whatever you’ve heard, monogamy is the only game in town for ...

Book Excerpts From 251+ Dating & Relationship Regrets by Bart Smith


Relationship Regrets 

Introduction & Welcome Message

251+ Dating & Relationship Regrets Book Excerpt
Copyright © 2024 by Bart Smith
Reprinted by permission.

They say, if you don’t learnnnn from the mistakes of your past (or the experiences of others), you’re doomed to experience them yourself sooner or later or even repeat them. No one wants to regret anything especially in the areas of dating, having sex, and/or getting married. Right? Those regrets can weigh heavily on the heart, consume your thoughts, put a dent in your finances, zap your energy, when you could be pursuing happier moments in a life with someone better suited for you.

Are regrets avoidable? To some degree, absolutely. Before we get into the hundreds of regrets people experience, I’d like to focus especially on regrets both men and women have experienced before, during, and after dating and their relationships. Many of these were probably the result of NOT following some advice given to them by others, online articles, or something you read in well-intended relationship book such as the one I’ve just written.

I recommend you read (or listen to) my other relationship books cover to cover. They are: Find The One For Me, Where Are You & Where Art Thou?, Laws Of The Bedroom, Watch Out Ladies, Wake Up Ladies, Fantasy Boyfriend and even B.S. The Book. I know they will serve you well, not because I am the author, but because I’ve researched at least 251+ relationship regrets that can be linked to things I’ve experienced, and some the hard way, as well as others, so I’m sharing what I’ve learnnnned. I am confident that you will benefit from reading all three books since they cover many topics that will enhance your life.

Now, let’s talk about the 251+ dating and relationship regrets that you’ll find inside this book. For starters, take time to read each experience from start to finish. Imagine what it would be like if you were to wear someone else’s shoes who is going through a rough patch in their relationship. Can you relate? Probably, because we all make mistakes.

Maybe you’ve experienced something similar. What were your circumstances? Do you regret the event ever happening? Heartbreak is painful and stress and misery can be hazardous to your mind and your body. If you knew what to avoid when starting a new relationship or the pitfalls of getting into a marriage without planning or preparation, wouldn’t you want to know more about these things? Regrets can be a good thing, especially when you can see value in learnnnning from your mistakes, but regrets aren’t just about what you did. One can also regret not having done something.

No matter what your situation is, where regrets are concerned, you are NOT alone! We ALL regret doing (or not doing) something in our relationship experiences. We’re ALL human after all. The objective here would be NOT TO REPEAT what YOU OR others have experienced. Trust yourself to do what’s right and don’t have any regrets.

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The Top 21 Relationship Regrets Men & Women Have With Dating, Sex & Marriage

251+ Dating & Relationship Regrets Book Excerpt
Copyright © 2024 by Bart Smith
Reprinted by permission.

1. Not taking things slower and rushing into having sex, moving in together, getting married to soon, etc.

2. I regret having sex with him/her, and not insisting we make this more than just hooking up. I had feelings for this person. If feelings are involved, sex isn’t enough.

3. Not listening (and following) their gut instincts about what they should really do and then acting on what their gut tells them. Forget friends, family and anyone else telling you what you should do. What does your gut tell you? Follow it!

4. Thinking they can change the person they’re dating/marry. An impossible task, to say the least. Don’t even try. Don’t even go there. Only the other person can change him/herself.

5. Finding someone who shares your interests and supports your dreams. Only the opposite type of person will crush your dreams and sentence you to a relationship prison sentence filled with dashed hopes and dreams.

6. Putting work/career first and their relationship second or last. Work will always be there. People won’t. Family members won’t. Memories worth making and remembering are those you make with the one you’re with, your children, etc.

7. Not asking someone out when you had the chance. Not only do you snooze, you lose, but you suffer the pain of regret for the rest of your life wondering WHAT IF you had asked him/her? How would it have turned out? Now they’re gone and so is the opportunity to find out.

8. Making a bad first impression or pushing too hard blowing your chances for a second date or further potential. Somehow, something you did or said really turned them off when you first met them or spoke to them over the phone. Take things slow, think before you speak, prepare your wardrobe and make your very first best first impression. Less is more. Especially when it comes to conversation. Ask more questions and stimulate the other person you’re interested in with fun questions to get them talking about their favorite subject = THEM!

9. Not taking enough chances to get out there and/or to meet people. Whether you’re tied up with work, or a couch potato playing video games 30-50 hours per week. GET OUT THERE! No one’s going to come knocking at your door to ask if you’re available for dating. YOU have to get out there.

10. Wasted time dating the wrong people. Somehow, you didn’t do a good enough job at vetting these wacko weirdo crazies. Instead, you justify staying with some line of B.S. only to torment yourself for months, even years. GET OUT of that relationship NOW!

11. Not taking time for yourself between relationships to recoup, he-tox/she-tox, and more. So true. Take a break. Regroup. Get the last relationship out of your system and prepare for someone totally new to walk right into your life.

12. Settling for less than you deserve. Why settle? Go for someone who complements you, makes you a better person, makes you smile 24/7/365. Nothing less. Understood?

13. Spending too much time in self-pity, beating yourself up, and feeling guilty about something in the past. Right this second, I want you to forgive yourself and forgive the other person who wronged you (if they did). Now, I want you to forget them and move on. Get in your car and just drive away!!!

14. I regret stringing him/her along. I should have been up front, honest and told her what I was/wasn’t looking for so they could decide to stay or leave the relationship to find someone more suited for their needs/wants/desires. Yup, can you relate?

15. Unrealistic expectations, wanting too much and thinking the other person would complete you. Completing YOU is YOUR job. You should only enter relationships when YOU are HAPPY inside due to your own perspective on life and how you live your life. Never enter a relationship thinking the other person is going to fix or complete you. No.

16. Wasting your time dating/marrying the wrong person because you didn’t put in the effort to really finding someone best suited for you. Never pick someone just because they’re the first person to come along in awhile. Sure, evaluate them, but chances are, they’re sent to you to grow you, not for you to get on their bus and ride the road of life with.

17. Not insisting on full transparency regarding finances. (i.e., how you and your spouse earn/spend/save money). This is a MUST, especially for women. You don’t need a prenup to say, “If I don’t have 100% oversight and learnnnn on how we handle our finances, I’m not marrying you. I want to know. I have a right to know. You have an obligation to share everything with me. In case something happens to you, I want to be protected. Again, this is non-negotiable.”

18. Putting the other person first and not looking out for your own needs, wants and desires. You can’t keep putting the proverbial oxygen mask on everyone else and not take care of yourself first. You heard it, now do it. Take care of you and others. You first, though.

19. No communication, not speaking up, not expressing your feelings or hearing the other person out too. You have a right to be heard if you’re hurting inside or you have questions or concerns about how your life is being impacted by someone you’re having a relationship with. If you’re not heard, if you don’t speak up, you won’t be heard. If you’re not heard when you speak up, then you need to shut up, and walk away from that relationship forever.

20. Didn’t try hard enough to save the relationship. This can be the case if you’ve neglected your duties to contribute to the relationship, and the other person decides they want out due to your lack of participation, inaction, abuse, and/or attention. If you want to save your relationship, do what’s right. Don’t go down without a fight. Make the proper changes to yourself or whatever’s falling apart. At least you can always say you tried to keep it together.

21. Didn’t leave the relationship sooner when red flags and signs started showing. This is the ultimate of regrets. Everyone should know, with time, you can only spend it. You can’t save it, borrow more, ask for more, do things over, etc. Once your time is spent, it’s spent. I have a saying, “Either way, you’re going to feel the pain. So, do the right thing that benefits you the most.” In this situation, LEAVE.

So, how’d you do? Did you see or relate to any regrets in that TOP 21 RELATIONSHIP REGRETS list? Who doesn’t at some point or another in their life, right? Remember, there are 200+ more inside my other companion book, 251+ Dating & Relationship Regrets Men & Women Have With Dating, Sex & Marriage. Check it out!

WOW, is all I can say. What about you? Knowing all the regrets that could happen to us in our pursuit for love and romance in our life, I know for me, I’m going to do my best not to repeat any of these regrets. Hence, why I wrote this book for you and for me.

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Dating/Relationship Regrets #52-72 You Too Should Avoid ...

251+ Dating & Relationship Regrets Book Excerpt
Copyright © 2024 by Bart Smith
Reprinted by permission.

52. “I regret leaving the relationship on bad terms and saying the things I did. Our last moments together were filled with yelling, screaming, name calling, throwing things and well ... it didn’t end well. I could have been the bigger person and kept my cool. That’s how I would have chosen to leave the relationship if I could have a do-over. Not that I want to. Granted, sometimes it’s normal to feel upset when breaking up. Emotions are at their peak. I just wish I hadn’t said the things I said. They were cruel, hurtful. I’ve learnnnned that I will handle my next relationship so much different and should there be a break up, I’ll act like an adult.“

53.  “I let my fears of whatever stupid thing I was thinking prevent me from saying, “I love you,” until she was dying and it was too late.”

54.  “I regret losing my virginity to someone who really didn’t care about me. I should have at least waited for the right guy to come into my life who would have been a little more patient.” (SUGGESTION: Read my other book, LAWS OF THE BEDROOM, while you wait for the next guy to come along you care about. Learn what you deserve and how to be treated inside and outside of the bedroom.)

55.  “I regret being in love with someone, dedicating myself to that person only to discover that I didn’t love him at all.”

56.  “She was the one who got away. I would sit/stand next to her every day (i.e., on the subway/at work/etc.) and I never asked her out. But a year ago, she started dating some guy and they’re now engaged. I feel like I blew my chance. That could have been me. Not again.”

57.  “I regret having children with this man. He’s so mean and self-interested. I do all the work. I’m not his maid/cook. I knew before we had children, something in my stomach told me something wasn’t right about being in a relationship with him. Now, I have to stay focused on the kids and divorcing him will be the best decision I can make. I wish I had listened to myself, trusted my instincts, and not had sex with him when he asked for it. That one night in bed changed my life forever. Forever, I will be linked to him because of our children although walking out the door with them in tow ensures I will eventually have a happy life with someone who genuinely cares about me (and them).”

58.  “I regret leaving a good thing when I had it. Since then, I’ve had a hard time trying to recreate the magic I once had (with him/her) and walked away from. Now, I spend less time looking back and more time looking forward to meeting someone new for me. When I find that new person, I think I’ll hold on a little tighter.”

59.  “Dating when I was in a vulnerable state of mind and then, staying in that relationship for a year because the person I dated was an emotional wreck, draining my energy, when I wanted out.”

60.  “Not being able to leave or move on. I could never muster up the courage to leave the awful relationship that was absolutely destroying me on the inside. I was depressed for years. My job suffered as well. Eventually, my mom stepped in and helped me escape. Love you, Mom.”         

61.  “I regret not following my grandma’s advice, which was, ‘never hurt a girl.’ What she meant was don’t hurt her on the inside (not just the outside).”

62.  “My regret and advice is to try not to leave your first boyfriend or girlfriend. What our first loves do to our hearts and minds really lasts the longest. Sure, sometimes you have to move on, but think about it. If I had been a little more mature, I wouldn’t have made so many mistakes. Now, if that first one that you thought was perfect didn’t work out for you, don’t spend the time going forward comparing possible suitors to him/her. Everyone has a first love and not all of them are lasting. If you both believe that you are good for each other, be smart and don’t take him/her for granted. Cherish what you have and watch it grow.”

63.  ”I regret doing everything together and neglecting ‘me time’ doing those things we enjoyed separately. Sure, you can be happy together, but to survive and thrive as a couple, encourage each other to create a mix of time together and time apart. It’s healthy for any relationship.”

64.  “Not putting an end to his criticisms about my weight constantly or how I should dress, not visiting me when I was hospitalized, when I sought therapy for my depression (which he caused), he was never there for me with phone call, support and much more.”

65.  “I regret not following through and leaving him even though he threatened to kill himself if I did. If he’s crazy enough to kill himself, I should have read the signs that our relationship was in serious trouble. I should have made my move sooner. I recall a time standing over the Grand Canyon when he told me that if I left him that he’d jump and take me with him. Was I blind to the fact that he needed help? He scared me and I should have run away. Why did I hang around? Anytime you are feeling threatened and unable to fix serious emotional problems ... RUN, don’t walk!”

66.  “I regret forgoing my own happiness to accommodate him and his needs. It totally backfired on both of us. We both suffered and were forced to make some hard decisions.”

67.  “I regret rejecting some pretty nice potential lovers because they didn’t meet all 999 of my personal requirements. I expected too much when looking for the ’perfect’ person to marry. I’ve learnnnned to allow myself a few basic requirements and to let the small things slide. I’m not going to be too picky anymore and I won’t put pressure on myself to accept/reject someone or pressure on him to be perfect. It goes without saying, he should be financially stable - as in - employable, in good health, have a pleasant nature, can make me laugh, and knows how to cook because I can’t although it’s never too late to learnnnn. A good relationship is give and take and mostly giving!”

68.  “Not having more fun with my wife. I let things fall into a routine and grow extremely boring. Years flew by and nothing changed. No wonder she left me. Gonna be more fun next time. More adventures, more spontaneous, more surprises.”

69.  “I regret sleeping with my ex. We broke up for all the right reasons. Now, she’s pregnant and I don’t want to be with her, again, let alone raise a child. Yikes. I should have gone jogging to run off my sexual frustration or even fantasized about sleeping with her; much safer. Whether she tricked me or the condom broke, either way, I’m in a situation, a game changer, I regret getting myself into.”

70.  “I regret not finding someone who fit my non-negotiable criteria (which I was unaware of), which is kindness, thoughtfulness, romance, affection, and someone who doesn’t burst into uncontrollable rages of anger and hostility. Someone capable of hurting me deeply, both emotionally and physically, cannot be on my list. No way.”

71.  “I regret not communicating with her because I was afraid to face the fact that we really weren’t compatible or a good match. Not speaking up resulted in years of despair and dissatisfaction when I could have made the effort to try to fix things.”

72.  “Listening to and believing the lies that ‘no one else will love me’ or ‘you won’t survive out there without me’ crap. What B.S. I was the fool who finally broke free of his bull.”


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Dating/Relationship Regrets #152-182 You Too Should Avoid ...

251+ Dating & Relationship Regrets Book Excerpt
Copyright © 2024 by Bart Smith
Reprinted by permission.

152. “I forgot, what follows friends with benefits -- a potential serial cheater? Even open relationships are risky when you‘re both playing musical beds. Whatever you’ve heard, monogamy is the only game in town for a lasting, loving relationship.”

153. “I regret putting my work over my relationships. I missed a lot of moments with people I dated, for sure.”

154. “When I didn’t stand up for what I knew deep down to my core, I screwed up and many times. I realized that I was pimping myself out by being available for every booty call and saying yes when I really meant no. When I finally got smart and assessed my value to myself and to others, I pulled out all the stops and put an end to the ‘I’ll let you know’ replies or ‘we’ll see’ comments or ‘maybe next week.’ I had to learnnnn to say NO. I’m over hooking up. I’m better than that. No regrets here.”

155. “I regret not asking her to dance. She could have said, ‘Yes!’ If she did, I could have asked her the next question, ‘Can I call you sometime? I’d like to see you again.’ How easy is that?”

156. “I wished I would have dated more in my early years. Instead I wrapped myself around video games, hanging out at bars and blowing money from my pathetic paycheck. Now, I have to play catch up on my love life, career, and more so I have something to offer someone when he/she comes along.”

157. “I’m tired of the bullsh*t that women must be strong, independent, powerful, and other social media crap that bombards us. I’m human and I sometimes ‘I’ feel vulnerable and weak, but that doesn’t take away from my strength or confidence in myself, as a guy. Looking for love is a natural thing, but the hype I hear about what women want makes me feel like they don’t need us men. Sure, women are still demanding gender equality and the feminist movement is still burning their bras, but at what price to their heart? The good news is women are climbing ladders of success like never before; whether it’s with a career or their own business. There are studies that tell us, though, how accomplished women are less likely to marry and every year she waits, the likelihood of marriage decreases. Those don’t sound like good odds. I now know what I want from a relationship ... communication, discovery, intimacy, smiles, growth, respect, journeys together and I won’t settle for less because I don’t have to. I bet a lot of women regret that it takes this long to figure out.”

158. “I regret not having more fun or taking more chances. I was the only one taking the initiative and bending over backwards to please that other person.”

159. “I regret not looking for ways to fill our relationship with fun, joy, and fulfillment once the chase was over. I tried to always be romantic by proposing to her daily until she finally agreed. Then we relived the honeymoon over and over, continued with date nights, and I thought we would be the forever couple. What I didn’t see coming was that I was making it all about me and she was along for the ride. Well, she finally rode out of my life.”

160. “I regret being hard on myself for being single for so long. I had to come to terms with why I was still single. I got some professional help to work through my issues and personal development. I now know that someone is going to walk into my life because it’s what I want and what I deserve. Odd that I had to learnnnn that there’s nothing wrong with being single. At least now, I feel prepared and excited about the possibilities.”

161. “I regret asking other people about my relationship when I was in trouble and needed advice. They really didn’t need to know my business and frankly they were biased and judgmental. I regret not trusting myself to know what I had to do.”

162. “I regret all the casual flings I had because they’re all contacting me through social media and asking, ‘How about tonight.’ What does that say about me that people are only interested in me for one-night stands? I’ve decided that I’d rather have 1,000 one-night stands with ONE person.”

163. “I regret being one of those immature, emotionally unavailable, rude, self-centered, and uninterested individuals who turned away most people. Someone finally leveled with me and told me what a shallow jerk I was. Ouch! I’m glad that I listened.”

164. “I regret pursuing someone who TOLD ME up front he wasn’t interested in anything serious. I should have taken him at his word and walked away. Instead, I thought I could win him over. Big mistake. I’m no longer going to feed off the bread crumbs of affection hoping that someone will change when they probably won’t.”

165. “I regret waiting for someone to come into my life when I should have been more proactive. Because of my inaction, I wasted years and opportunities to hone my social skills. I should have gotten out there and practiced a little, engaged with others and improved my odds at finding someone.“

166. “I regret not treating my body, mind and heart like a billion dollar bank account. With a bank balance like that, I’d keep that under lock and key. You’d have to be very, very special in order to get access to my funds or me! I am priceless, precious and my body is sacred. No one can make withdrawals without my permission if you know what I mean.”

167. “I let someone convince me that I should get an abortion and that I’d feel okay about it afterwards. Biggest regret of my life. I should have had the baby, and decided what to do with it afterwards. (i.e., adoption, keep it, let my aunt raise it, etc.)”

168. “I regret not leaving the relationship immediately when jealousy surfaced time and time again. I couldn’t go anywhere or do anything without being monitored. I had to be accountable for all of my actions. It was like being under house arrest. That’s no way to live.”

169. “I regret not letting the other person know where I stood when we first met. Yes, I enjoy having a few drinks, making out, even sex with the right person, but I disregarded the fact that I was also in a relationship with someone. I cheated on everyone -- the person I was in a relationship with, the person asking for more, and myself. Everything is wrong with this picture. I needed to STEP UP my game before I caused more harm.”

170. “I regret not giving my husband more space so he could spend quality time alone, with friends, his hobbies, etc. I confess to always nagging him. I constantly interfered whenever he made plans for himself. Finally, he left me. I really hope he’s happy because I’m not. I made such a mess of things.”

171. “I regret not seeing the signs leading up to our wedding day, and then at the reception watching her get drunk and throw tantrums. What did I get myself into ? I should have seen the signs that she had issues and called it off. Instead, I’m dealing with a person with problems that I can’t fix and she’s not willing to talk about them. How we lasted for any length of time I don’t know. We finally divorced. Two years of hell when I should have listened to my gut. Yes, I have regrets!”

172. “From a woman’s perspective, it’s okay if you make the first move. Gone are the days when women need to wait for men to make the first moves, propose, and more. I lost a really great guy because I didn’t approach him when I had the chance.”

173. “I regret not insisting/pressing the point that I wanted to be in a serious relationship. I never shared this. Well, no one is a mind-reader, but these are things that you should gradually work into because how is he/she going to know how you feel about getting serious or not?”

174. “I regret saying that I’m not looking for anything serious when I’m trying to avoid someone. Make yourself available to those you want to attract and discourage others by being honest.”

175. “I regret pushing my friends away and making him the center of my world. In doing so, he took me for granted and I lost myself in the process. I still feel damaged and unable to move on. I need to do some repair work with my friends as well as myself.”

176. “I regret not asking about our finances. When we divorced, I had no money because I didn’t ask when I should have.”

177. “Forcing her to watch porn with me ruined our relationship. Porn isn’t the issue. The addiction is. Sex should be a good thing and not exploited. Nothing good comes from that.

178. “I lost all my friends. My boyfriend hated them and resented me spending time with them even though I tried to include him. So, I lost them. Now, who’s the loser?”

179. “I regret hooking up as much as I did and friends with benefits never works. It’s a playing field for jealousy, disenchantment, loss of self-esteem, and more taking with less giving. I want full-time company, companionship, a confidante, a future, potential for a much deeper connection. That doesn’t happen when they leave the next morning.”

180. “I regret wasting so many years believing I wasn’t good enough for someone, or not good enough for happiness. The opposite is so true. I am worthy. I am good enough. I am happy, now! Feeling sorry for myself was such a waste of time. Who out there is looking for someone positive about life like me? I’m right here!”

181. “I regret giving up on all my dreams, passions, goals and personal desires just to keep her in my life and happy. I was unhappy all that time and she wasn’t happy either.”

182. “I regret pursuing and allowing myself to be involved with a married man/woman. I can’t help but think that I caused their divorce. Sure, they had their problems, but did I have to be the straw that broke the camel’s back? If someone interests me and is in the process of divorce, give it at least 3-6 months because it takes time to heal. You can still befriend the person, have lunch/dinner with them, but don’t push to have (rebound) sex before starting a new relationship and taking things slowly.”

183. “I regret that I confused sex with romance. I want both so I’m holding out for both. I want to be crystal clear with that someone. I want the desire for sex with him, emotional attachment, even love and commitment to a relationship. I want to share my bed with only him and wake up with him every morning. Ideally, I’ll find someone who wants the same thing. I can wait.”

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