Lovesplaining
Lovesplaining with Evan Marc Katz
Mailbag #5 - Aging, Money, and SO MANY Dating App Questions
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Mailbag #5 - Aging, Money, and SO MANY Dating App Questions

The mailbag to end all mailbags!
Brad and I are going to be collaborating during my summer break.

Thanks for being a part of Lovesplaining. This is my final mailbag for paid subscribers but I’ve decided to give it to everyone for free. Why the hell not?

Anyway, if you enjoy my work here and want to stay connected, please:

  1. Take my quiz to get my free newsletter

  2. Subscribe to the Love U Podcast

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And now, enjoy this month’s amazing questions from our readers:

Jeanne M

You say that we should not start dating until we feel confident. I feel as though I am confident in my decisions to let men go when they show me they are not a “good intern” (I might be too good at this). BUT, I’ve always struggled with confidence in my physical appeal to men and sustainability of my physical appeal as a relationship develops. I grew up in a very critical family focused on appearance. Now that I am 52, and aging is happening, I continue to struggle with this, ESPECIALLY when I am interacting with a man that I am attracted to and there seems to be potential in the other categories as well. This has been a lifelong struggle that no amount of “work” has resolved. I would appreciate any guidance you are willing to share. Thank you for all that you do 😊.

Dana

Hi Evan, I'm finding that even after having a great 45 minute/1 hour phone or video call with a man from the dating apps, he still proposes coffee as our first in-person date. I'll let him know that I think it would be more fun to meet up for dinner or happy hour at a place we've been meaning to try, but there are lots of men who still don't get the hint. It's happened a few times now. Do you have any suggestions on how to phrase/wordsmith my request for a first date that isn't coffee?

Annie M. 

If men are more vulnerable and open up more after physical intimacy, and as a woman, I need to feel the emotional intimacy first, how do I reconcile that? I worry about getting attached to someone by being physically intimate, hoping the emotional intimacy will deepen, but what if it doesn't?

Cokie

I still struggle with how to start a conversation on a dating site. Do you think if the man is interested, it doesn't matter so much what I say but just that I reach out? I feel weary sometimes trying to be clever or funny and prefer just being sincere. Help please.

Janell 

How low effort of a profile is too low effort to engage with? Some of these guys have almost nothing on their profile - but they might have a couple of things that show potential- such as level of education and a few common interests. So do I message? Or do I weed these low effort profile guys out?

Felisa 

I would love to hear your ideas on transitioning off the app. I get a fair number of matches but getting them to become dates is an ongoing challenge. Many of the exchanges just fizzle even though I try to craft interesting questions to lead towards that but I also am not comfortable asking a man out. 

Greta

I’m dating someone with employment issues. He just lost his job. He also has three kids. I have really loved him but worried about our future together. He’s a sweet guy but we do not have the same ideas about money and I’m worried about being a stepmom to his kids…

Rita

I am curious about 2 things:

1- How do you suggest screening guys on apps to make sure it's worth actually meeting? I have had around 14 first dates (10 in the last 5 months), and only 3-4 of them were guys I would have gone out with (2 it wasn't mutual, apparently). If a guy suggests getting together for coffee or a walk, should you always insist on a video chat to see how the conversation goes? I feel like you've probably answered this question a lot of times before, but I'm not finding success.

2- What are your thoughts on googling someone before you meet or finding out they googled you? I have a fairly extensive digital footprint, and recently a guy I had a phone call with figured out who I work for (it wasn't hard, given my small city and uncommon employer), then found my last name and did a deep dive. He told me about it on the phone, and I was amused and a little taken aback.

Liliya 

When you mutually decide that a long-term relationship is not possible and the guy wants to stay friends, what does it mean? He also found another woman he is pursuing a relationship with.

Jill 

I met someone last week for a date. We had a nice time. At the end of the evening, he put his arm around me and rubbed my back. I flinched. We emailed a few times and he said he didn’t feel any chemistry. 

1. I was told that if we had a nice enough time to go on 2nd date 

2. At what point do we come off more as a friend? When and how do we evaluate we are doing something wrong? 

3. I was married for 30 years so the process is new. I didn’t want someone to touch me on 1st date 

4. Loss of confidence when you are ghosted or “rejected”

Subscribe below to watch me answer ALL these questions.

Lovesplaining is reader-supported. To receive new posts and get access to more content, coaching, and community, please consider becoming a free or paid subscriber.

I appreciate you and hope that my answers give you some clarity - not just about your issues, but about how others’ questions apply to you, too.

Evan

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This Week's Love U Story

I am so excited to finally be writing you about my dating success story thanks to your help!

I have been following you since 2014 and am also a Love U student/graduate! I think you are such an awesome dating coach! I tell anyone who will listen about you, your websites and your books! Yes, I am an avid student and fan! Even more so now that I am in a relationship and exclusively dating a man I met online. By following your suggestions everything happened just as you said it would.

I am a divorced 53-year-old, highly educated successful and independent black woman with an MBA and a high paying job with the Federal Government who knows the value of having a man in her life! I was married for 22 years to a man I met when I was 18 and a freshman in college. After 8 years of marriage we had one child, a daughter, who is now almost 20 and a sophomore in college. We divorced (when she was 13) due to growing apart and not having the same life goals. It was a very amicable divorce and we are still friends.

After my divorce. I allowed myself to be used and abused and got my heart broken. It was during this time, that I found you and signed up for Love U. Taking your course gave me the courage to leave that non-relationship and work on myself and build my self-esteem. I sincerely thank you for that! I did online dating since the very beginning of my divorce.

Of course, from you, I learned that you never take a break until you find someone. This last time, as soon as I got rid of the ridiculous items on my long list of requirements and became a paid member, someone found me in less than a month!

He is family oriented, kind, generous, funny and treats me like a queen. He is tall, has grey hair, is muscular and has the sexiest blue eyes ever. We have so much in common, it is unbelievable. Initially, I did not have butterflies when I first met him and I didn’t think he was my type. He has grown on me and now after almost 2 months of dating, I get butterflies looking at and thinking about him. I find him to be the most sexy and romantic man I have ever dated. This is all because I listened to you and took your dating advice! I have never been this happy in a relationship. Thank you, Mr. Evan Marc Katz!

Love,

LaVonne

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Lovesplaining
Lovesplaining with Evan Marc Katz
Are you the woman who has everything except your man?
Evan Marc Katz is a dating coach who has specialized in helping smart, strong, successful women since 2003. He has written four books and has been featured in hundreds of media outlets, including Today, the New York Times, and CNN. Since 2015, Evan’s blog has had 35 million readers, his Love U podcast has 2.5 million downloads and 13,000 women from 40 countries have graduated from Love U, his six-month video course that helps women understand men and find love. Evan lives in Los Angeles with his incredibly cool, incredibly patient wife and their two surprisingly funny children.. www.evanmarckatz.com/apply