Posts in Dating
Not settling for good enough

Dear Lori and Jeff,

I’m 31 and still searching for a partner to share my life with and to start a family. I’ve been in several longer-term relationships since college but none of them have felt like they had any real lasting potential. I don’t want to sound conceited, but it seems like the caliber of available men these days is not what it used to be. I want a man who takes care of himself, provides for himself, is a genuinely good person and is ready for commitment. The men I’ve met seem less motivated to work, and less confident in who they are and where they’re going in life. I’ve decided I won’t settle for a partner who doesn’t measure up just because I’m ready to take the next step. Am I selling myself short?

Signed, Searching for a Man

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What you do on a ‘break’ can fracture a relationship

Dear Jeff and Lori

I had been dating my girlfriend for eight months when we decided to take a break in October. I love her, but we’ve had a few key problems from the beginning. We got to a point where we didn’t know how to stop arguing over these issues and thought a little time apart would help us re-center and get a little clarity on what we needed to make the relationship work. I went to Mexico with the intention of doing just that, but met a really cool woman while I was there. We spent a few weeks together and part of me is interested in getting to know her more. My problem is that when I came home, my girlfriend told me she loves me and is wanting to work on our relationship. I’m willing to put in the work with her to give it a real try, but I don’t know if I should tell her about this other woman I met. I won’t pursue a romantic relationship with her, but I don’t want to completely cut her friendship off either. What should I do?

Signed, Spill the Mexican Beans?

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My partner snooped through my phone. Is that a dealbreaker?

Dear Jeff and Lori,

I recently caught my girlfriend going through my phone. I gave her the passcode so she could look at photos from our trips together, not anticipating that she would continue using it to snoop. She says she has the right to know who I’m talking to and what’s being said. I’ve never cheated on her, but she has always been jealous of my female friends. I no longer have any contact with past casual hookups, but I’m not willing to cut off communication with other friends for my girlfriend. I believe a little privacy is healthy in relationships, but she is becoming increasingly insistent on having an all-access pass. Who’s right?

Signed, Over Her Shady Snooping

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Financially dependent boyfriend wants to move in

Dear Lori and Jeff,

My boyfriend and I have been together for seven months and recently he’s been advocating to move in with me. We have a lot in common and I appreciate that he helps me have fun. He’s also incredibly loyal and tells me all of the time how much he loves me. However, I’ve spent my 20s and early 30s building a successful career and becoming financially independent. He’s still “enjoying” life and has been slower to figure out what he wants to do. As a result, I foot the bill for most of our dates and vacations. I wouldn’t mind if he was in school or actively working toward a career, but he spends a lot of time on the couch. I don’t want to become his bank account. However, he insists that if we live together, he’ll be more motivated and I wonder if this is the opportunity he needs to get his life on track.

Signed, Cohabitation Hesitation

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Be honest with yourself before jumping into casual sex summer dating

Dear Lori and Jeff,

I’ve been single through most of COVID and am feeling ready to get back into the dating game this summer. As more people are getting vaccinated, the dating scene seems like it’s cueing up to be a feeding frenzy. My friends are talking about using the hookup-rinse-repeat cycle as often as they can fit into their schedules. That’s just never been me. I’m anxious that the people I meet will have expectations for casual encounters. My best friend said I should loosen up and just have fun for a few months. It’s hard enough that I’ve been out of the scene for so long, but this is just making me feel even more overwhelmed. How do I navigate dating in this scene and still stay true to myself.

Signed, Scared to Jump In

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Can't commit, wondering if there's someone better

Dear Lori and Jeff,

I met a guy about a year ago online. Both of us were pretty cautious about COVID and found ourselves becoming more distanced from friends who were less concerned and living life more freely. As a result, we ended up becoming each other’s main connection and support. If it weren’t for COVID, things probably wouldn’t have progressed so quickly. Now that the world is starting to open up again, I don’t know if I want to continue staying attached to him. There’s nothing inherently wrong with our relationship. I like him, am attracted to him and enjoy spending time with him, but I’m curious if there’s someone better for me out there. On the other hand, I’m worried about walking away from someone who might possibly be the one. Help!

Signed, Tempted To Try Something New

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What to do when dating apps aren't working for you

Dear Lori and Jeff,

I ended a two-year relationship a few months before the pandemic hit and so, for almost a year and half, it’s just been my dog and me. I’m now fully vaccinated and things seem to be moving back in the right direction for a bit more normalcy in the world and I’d like to start thinking about dating again and possibly finding someone to spend the rest of my life with. I’ve tried dating apps in the past and have been reading about all the different strategies online but they all seem very impersonal and formulaic. I know I have some less-than-ideal dating patterns from the past that have landed me some less-than-ideal men so I’d like to figure some of those out along the way. Do you have any advice for both dating strategies and to help me understand my past patterns?

Ready To Date

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Struggling with partner's fading career dreams

Dear Lori and Jeff,

My boyfriend is incredibly smart and studied hospitality in college. When we met 4 years ago, his dream was to be the GM of a luxury hotel. But in the time we’ve been together, he hasn’t taken any steps towards advancing his career and is still bartending at the same restaurant. He’s been hinting at wanting to get engaged, but I’m struggling to get past his lack of career motivation. I know he’s good at his job and makes good money, and I understand that going back to school can seem overwhelming, but he sold himself as wanting to become a powerful agent in his industry. Now he just complains everyday about the long hours on his feet and the rude customers he had to serve. I’m not sure I want to commit my life to this, but I do love every other aspect of him. What should I do?

Signed, Wanting Him to Aspire

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Girlfriend not making enough time for me or relationship

Dear Jeff and Lori,

I love my girlfriend, but I’m really starting to question whether she can meet my needs in our relationship. We’ve been living together for 2 years, and over the last year it seems like I’ve slowly fallen further down her priority list. I feel like I’ve been doing a good job of clearly and kindly asking for what I need, including more time together, and to be included more in decisions. But she has started to respond with frustration, saying I need too much from her. I know she’s busy with work and taking care of her parents, but she also makes time to ski and hike with friends. Since the pandemic started I’m able to work from home with a flexible schedule and think it’s a great opportunity for us to be together more. How can I help her see that the focus should be more on our relationship?

Signed, Wanting More

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Missing physical touch during pandemic online dating

Dear Lori and Jeff,

Physical touch is my love language. I’ve always used it as a way to test my level of interest in a guy—resting my hand on his leg, casually leaning up against him, even initiating the first kiss. That touch, and his response to it, was often my chemistry litmus test to assess how close I wanted to be to someone. But now with online dating, I’m struggling to gauge my interest in them. Even when I finally get to meet some of these guys in person, physical closeness is still off-limits. I’ve cycled through half a dozen guys in the last few months and am feeling more confused than ever. I want to be in a relationship but I don’t know how to get there when I’m six feet away. Help!

Signed, Out Of Touch

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Don't stay in a relationship just because of the pandemic

Dear Lori and Jeff,

Over the past few months, my girlfriend and I have been realizing that maybe our relationship is nearing its end. We’ve been together for two years and still really care about each other, but neither of us has been really happy since the summer. We’ve both threatened to leave during arguments, but the truth is that going through a breakup and being single during a pandemic doesn’t sound great either. Do you think it’s wrong to stay together until the world gets back to some semblance of normal?

Signed, Waiting It Out

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What to do when mom doesn't approve of girlfriend

Dear Lori and Jeff,

I’ve been dating my girlfriend for about two years and I think I’m ready to make a deeper commitment. We enjoy our time together, have a lot in common and have a good balance with time spent apart with our careers and individual interests. The only problem is that my mother can’t seem to accept her and approve of our relationship. She says things like, “Are you sure you’re ready to settle down?” and “Do you really think she’s the one?” but I suspect it’s more about the fact that she thinks my girlfriend isn’t good enough for me. She has recently started making subtle comments in front of my girlfriend. I feel really awkward when this happens so I try to just brush it off, but my girlfriend has gotten upset with me for not standing up for her. She says I need to resolve this issue before we move forward with our relationship. I feel stuck between the two most important women in my life. What can I do?

Signed, Rock And A Hard Place

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How to know if a relationship is moving too fast

Dear Jeff and Lori,

I'm struggling with letting my guard down in my current relationship. We were both recently separated from our spouses when we met, and he moved in with me very quickly during the first COVID lockdown. Both of our marriages were unhealthy, and I moved quickly to file for divorce. My partner, however, has a son who has been very open about his disapproval of his dad’s choice to leave the marriage. My partner says he is fully committed to me and has proposed, but is afraid that filing for divorce now will sever his relationship with his son. I also know that he’s in regular contact with his wife, and that she still wants to make the marriage work. I feel so insecure right now and keep asking him to finalize his divorce. Am I wrong to feel this way?

Signed, Insecurely In Love

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How do I know if she is the one?

Dear Lori and Jeff,

My girlfriend of 3 years is dropping some not-so-subtle hints that she’s ready to get engaged. She’s great and I love her, but I’m not ready to make that commitment to her yet. I’m not totally sure why. I’m in my mid 30’s and it’s not that I don’t want to settle down, in reality I feel like I’ve already done that with her in this relationship. I’m just not sure how I’m supposed to know if she’s the one I’m meant to be with for the rest of my life. I’m attracted to her, and we have a lot in common, but not everything. I feel like I should just know if she’s the one, and I don’t. What do I do?

Signed, Is She The One?

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Age gap in dating: what's too old?

Dear Lori and Jeff,

I’m 36 and think I’ve finally met the man of my dreams. He’s handsome, kind, funny, sensitive, has a great career and knows what he wants in life. The only problem is that he just turned 50 and I’m worried that our age difference is going to be an issue further down the road.

Signed, The Younger Woman

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Avoiding dating because afraid of making the same mistakes

Dear Lori and Jeff,

I quickly fell in love with my college sweetheart and we married right after we graduated. The marriage slowly deteriorated and we hung on for much longer than we should have. We finally ended things and I’m now a year out from the divorce. I feel like I’m ready to meet someone and have been dating for the last few months, but I’m so overwhelmed. I’m afraid if I connect with anyone I’ll fall too fast and make the same mistake again. So after a few dates I’m finding myself pulling away or coming up with excuses to cut it off. I really do want a relationship, but won’t let myself get attached. Please help.

Signed, Once Bitten

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Boyfriend pursued me then stopped putting in any effort

Dear Lori and Jeff,

My boyfriend and I met a year ago through mutual friends. I wasn’t interested in dating anyone at the time, but he put an incredible amount of effort into convincing me to give him a chance. He sent me cute little gifts, surprised me at work with lunch, and talked about the places he’d like to take me. I caved and eventually agreed to date him. The first few months together were exactly what he promised; romantic dates, thoughtful surprises, and fun adventures. The energy he was putting into us really inspired me to bring my best self as well. But after I became invested in the relationship things started to shift. He gradually got less romantic, and now the tables have turned so I’m the one that is always having to plan things. For months he hasn’t been the romantic guy he sold himself as. What do I do?

Signed, He’s Phoning It In

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Don’t jump into cohabitating because of COVID

Dear Lori and Jeff,

I have three roommates and my girlfriend has her own place. Before the pandemic, we’d never really talked about moving in together, but I spent most nights at her condo. When the stay at home orders hit, we decided it would be best if I temporarily moved in with her. We’ve gotten along great, and I’ve been hinting that maybe we should make this a permanent arrangement. But she says she wants to be more thoughtful about making such a big decision, rather than just falling into it. What’s a healthy process for deciding if we should take this next step in our relationship?

Sincerely, Ready to Move In

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Are you single because you're too picky?

Dear Lori and Jeff,

My friends recently set me up with a guy and we went on a date a few weeks ago. He’s nice and seems to have his life put together, but I’m not really interested in him. I could tell that he was into me and said he wanted to go out again, but I didn’t feel the same chemistry. My friends think I’m crazy for not wanting to see him again and it’s gotten more complicated because they’ve started inviting him to hang out with our group. It’s becoming awkward because he keeps hitting on me. How do I get out of this gracefully?

Signed, Not Into Him

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When to end an on-again-off-again relationship

Dear Jeff and Lori,

I’m in my late 20’s and have been with my partner for 4 years. Twice in the last year we’ve broken up and gotten back together. Each time we decide to try again, it’s good for a few months, then one or both of us starts to question if this is really it. On paper, we seem like we’d be perfect together, we have similar interests, values, lifestyles and goals. We don’t have any big issues, but we seem to bicker all the time about the small stuff. I’m at a place in my life of being ready to get married, and I can’t do this back and forth with him anymore. I need to make a decision to go all in or get out for good. Can you help me figure out how to choose?

Signed, Should I Stay?

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