How to Date as a Single Mom

love u podcast

Dating as a single parent is like regular dating, with one massive complication that creates a bunch of minor complications. In this case, the complexities of an amicable vs. bitter divorce, a peaceful vs. contentious child custody battle, and the financial well-being of both you and the divorced dad you’re dating. Tune in to the Love U Podcast to learn five rules for single parent dating and hear me help two women get clarity on how to date as single parents.

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  1. 1

    The first caller’s dilemma was very interesting. Kudos to her for contemplating a challenging but also very necessary way of having children in her life. Fostering is not for the faint-hearted, and i understood why Evan was walking through the alternatives. I don’t know  what it’s like in the US, but  in my country  starting the adoption process at 39 is unfortunately not possible. If you haven’t started the long winded and hoop-jumping process by your early thirties your ship has sailed. Also, and this might be different in the US, being a prospective single parent is a tough sell towards adoption agencies who would rather place children in two-parent families. Finding the right man who would be a good match for you and a good father is also a challenge at any age, I can understand why at 39 she decided to take this route. It’s a route that has at least a more defined outcome.

    The political question, redirecting the conversation away from a potentially heavy topic, is something i am going to try when i go on a date! I regularly meet men that need an outlet with the heavy BS they meet in their lives and up until now i did not have a solution to that problem. Other women complain that they sometimes feel used for sex, but my experience has been feeling as if i i’m being used for venting instead of being treated as a light hearted and desirable date. By the end of the evening i feel like i should have charged by the hour! They quite often don’t have many friends, or the friends they do have aren’t in the market for that type of therapeutic listening. It introduces a heavy quality to the first date and i also wonder what they remember from their date after it has finished, after raking up so many negative feelings for the difficulties in their lives.


    1. 1.1

      Malika it sounds like your problem is more that you are being placed right away in the friend zone (that is venting zone). Try flirting more. Use their vents to flirt a little. It is the only way otherwise you will really be just an acquaintance or friend. Also nothing wrong with saying explicity “Ok let’s set any negative thoughts aside for this evening and let’s talk about something bright”. In other words, if they are all dark, try to be light as much as possible and don’t let them make you dark too

      1. 1.1.1

        Hi Ross:

        The subtopic has definitely made me think on how to tackle the venting in a constructive way and your tip is a good one. You have a point with the friend zone, I often in such situations revert to being the listening ear, as i am with my friends. But how i behave with my good friends who sometimes need my support shouldn’t be the same as when i am on a date! What makes it difficult is that in such a situation I find the negativity a turn off and a first date who wants to talk about his ‘positive addiction’ (ie his ex) isn’t especially exciting or  sexy! But as Evan and others have pointed out on this site, you can’t change the other, but you can change your own behaviour.

        1. Ross

          Maybe try being more proactive and do more talking yourself? I think a lot of people find it awkward when there is some silence and they will try to fill it up in whatever way they can even if it is a negative way.
          Also, if you detect a flow of negativity before meeting (while talking over the phone) then I would simply say it very honestly that you are are into positive people and wish them the best. If they are so negative, it must come out over the phone (voice, not texts) too and there you can avoid the drag of a face to face date.

        2. Adrian

          Hi Malika,

          If a person is venting negativity towards you on a first date then tell them. If they make attempts to change then that is a good sign, if they don’t or if they are offended then you now see what you need to see to decide that their will NOT be a follow up date.

          …    …    …

          As I get older I am learning that we as humans place such a huge importance on avoiding such titles as being selfish, but I am now starting to realize that some selfishness is good.

          When it comes to situations like the one you described in dating be selfish and put yourself first. Don’t try to intentionally put yourself in a negative atmosphere for a man you barely know.

          That is a sign of low self-esteem and low self-worth. Just because you are being kind to someone doesn’t mean you have a healthy self-esteem or that you love yourself; it simply just means that you are kind.

          Malika love yourself more and leave these guys (tell them why) but leave them. If a person isn’t trying to impress you and focus on you during the courting stages then how do you think they will treat you once you start dating?

      2. 1.1.2

        Hi Ross,

        Isn’t your advice to Marika a contradiction?

        If a man is friend-zoning a woman that means that any attempts by her to flirt will be futile.

        But I do like what you said in theory, I never considered it but what you say makes sense. When a person isn’t trying to put their best foot forward to impress you on the first few dates it is a sign that they are not really that into you.

        1. Ross

          For sure if either the man or the woman feels no attraction for the other, it is a mute point. But you can avoid many of these situation by building a connection over the phone or see if there is one, as well as exchanging some photos (and paying attention if they are airbrushed lol).
          Now, I read (and it is true in my experience) that you feel attraction or lack thereof in the first few minutes into the first face to face meeting / date. So it is good to set a positive vibe immediately and do some flirtations right away. Nothing major just a longer than usual stare, smiling a lot, maybe a big long hug at the beginning when you first meet. And continue during the date. If the other still vents negativity, lose the loser. But you still win because you know you put your best foot forward and you got to practice being a good first date, which will make you more and more awesome for the next dates.

        2. Malika

          I think it depends on the man. If he finds fault in everything (from his life choices to the way the waiter puts down his glass of beer), then i’m thankful i dodged a bullet and excuse myself after a couple of drinks. If he just seems to be hung up on one thing and he can be redirected away from it, you might be meeting someone with a lot of potential.

  2. 2

    I tried dating as a single parent and it just didn’t work. Lack of time and really no men interested. My last date was 10 years ago. Sad but oh well.

    1. 2.1

      That sounds rather fatalistic.   Maybe you just met the wrong men?   I am a single parent of 3 and I have dated for almost 6 years.   I will admit that most of my relationships haven’t been great but I learned from each of them – about myself and happiness.   My longest relationship was 2 years but I realized that he wasn’t the right person for me.   Had I not realized that I may have remarried but I don’t know that it would’ve worked.   I dated a man still in love with his ex wife for almost a year (my fault, he was an obvious commitment phobes)   and had a few more casual relationships.   My only regret is wasting too much time on men who obviously were not meeting my needs.   There are tons of emotionally unavailable and narcissistic divorced and single men (and women I assume) out there.   Now my kids are older and I am dating a wonderful man who meets all the things I have been looking for (almost).   He is divorced also,   a father of 2, loving and passionate, reliable, a planner, emotionally available, a home owner, financially secure (makes way more than I do), smart, similar politics, same religion, similar family background, handsome face, taller than me, most of his hair, sexually compatible.   Only negative?   A few extra pounds.   I am delighted that I found someone wonderful and didn’t give up.   There will be someone, don’t waste too much time on bad boyfriends.   A bad boyfriend will be a bad husband (if he ever becomes one) – just learn how to identify when someone doesn’t meet your needs and cut him loose.

      1. 2.1.1

        Well I’ll be an empty nester in the next couple years and really don’t want to spent the rest of my life alone but I don’t know what to do, I’ve tried online dating for months on and off, never actually met anyone, talked to 3 men for a  short time  but once they found out that I’m a single parent they shut things down and vanished.   Had some friends and family set me up but those didn’t last beyond a first date.  Met a couple single dads through my son’s friends – nothing. Someone actually told me “well the guys just don’t like you”.   Gee thanks that’s helpful!

        1. L

          Dandy, that sounds frustrating.   However, why are men hearing that you are a single mom after you have met?   That should be part of your profile.   When using a dating app, which doesn’t offer a drop down menu regarding parenting, I mention in my description that I am a mom.   I don’t say how many kids I have but people usually ask within a few chats.   This way, anyone who messages me knows I have kids.   I don’t get bombarded with messages and swipes  like other women of a similar level of attractiveness but without kids might, but I don’t care.   Someone who doesn’t like kids is a deal breaker for me.   Also some single dads prefer to date women with kids.   I would be honest up front and see what happens.    I am not saying it is easy – I have been single for almost 6 years – but I have found plenty of men happy to date me.

        2. L

          I mean, after you have spoken.   Men should know you are a parent before they message you on an app or dating site.

      2. 2.1.2

        Hi L: your message gave me hope. Single parent of four here , aged 10-15 and been single past 6 years. Dated as well but most men struggled with number of kids I had although none met them ever. You give me hope.

        I am strong, independent and yes I work two jobs to maintain our lifestyle, but I do make efforts to date. They very often wonder why there is no father on the picture or paying child support and I atppped sharing why because it wasn’t no pleasant.


        Where did you meet your current man? Online?

  3. 3

    There’s always two sides to every coin. I’ve heard many of my childfree facebook friends moan about dating new guys, and how they invariably run into some version of “Since you don’t have or want kids, you are probably a cold, selfish bitch” or “since you don’t have kids, you don’t understand”.

    1. 3.1

      Hi Nissa,

      I have had that happen as well.

      I have had that said to me (maybe not so crassly) by both men and women. People imply that since I don’t want children or since I don’t want to date someone with children then I must be selfish, arrogant, etc.

      Which is why I find it so funny that on the weekends when I get my toddler nieces and toddler baby cousins by myself without the aid of anyone else.

      When people see me out with them their first statement to me is “Oh, you must be a wonderful dad!”

      As my uncle once said: Perception is Reality.

      1. 3.1.1

        Hi Adrian & Nissa,

        It’s not fair to judge people who don’t want or plan on having kids to be selfish or irresponsible.   The few times I have had an opportunity to really talk in depth with someone about why they don’t want kids and how they made their decision, I found that their decisions were made after a lot of deep thought and careful consideration.   There were a few who just always knew they didn’t want to be parents, but for others the decisions flowed from circumstances in life. Hopefully you are able to ignore people when they say things like that.

  4. 4

    Thank Evan for the topic, and thank you for your honesty. I have been a single parent of two for 5 years now. I have been on dates. I’m very careful with who I go out as my time is very limited. My goal is to have fun, and in the process meet good people( I learn that from you ;)) I’m not looking for a dad for my kids, I’m looking for a companion for me. I have the pictures of my kids on the screen of my phone, so if the question is asked – it’s always asked – I say yes, I have kids, see the pics and move on to talk about him or me. I don’t talk about my kids on the date any more. Yes, there are men that never called back, and there are some that did. I have dated men with kids and without kids, and it has been about the same experience. I don’t believe is harder for me as a single mom to date than my friends without kids. The main difference is that I go on fewer dates than they do. I date once a week, they date several times in a week. I’m positive as I have met great people that we keep in touch. Thank you for your advice as I have applied it. It changed the way I viewed dating. I have been going out for the past 6 months with a guy with no kids. No introductions yet, as I want more time to see how it works out.

    1. 4.1

      Felicia’s story is always what I see.

      Single mom’s out with guys who have no children all the time.

      I guess that is why whenever this subject comes up I always wonder is it really so hard for single moms to date?

      A single parent will have the same handicap or boost as a women without kids.


      If she is attractive enough for a man he will ask her out regardless of the fact that she has children.

      1. 4.1.1


        I’ve been a single mom my whole adult life since I had my oldest son when I was way too young, and all I can say is that dating while parenting has it’s challenges.

        Yes, the more attractive a SM is the more men will be interested in her.   However, there will always be less men interested in her as a SM, than if she was childless.

        The age and life stage a woman and her male dating peers are at makes a big difference.   When I was in my early 20s there was a certain look of horror that would come over a guy’s face when he learned I had a son that I dubbed the “Oh my God what would my mother say!” look.   I’m positive  many young men took a pass on me back then because of it.   Or I got downgraded from an LTR prospect to a STR or NSA sex candidate only. (Although I’ve never been into the NSA thing)   That got balanced out by the fact that there are proportionately a lot of single people in the early 20s age cohort.

        At that time, I found that men who were from something other than a traditional biological nuclear family were more open to dating me.   Whether they grew up in step families as kids, were raised primarily by grandparents or relatives, or had been adopted.   I’m guessing that since they lived in what at that time was viewed as a different than “normal” family, they weren’t as phased by my different than normal status.

        Then when I got to my early to mid 30s, being a SM almost became a non-issue.   I only had one kid and my son was in his teens then off to college so I had free time and a potential mate  wouldn’t have to actively parent a young child.   Also there started to be more single parents in the dating pool due to people who married young then divorced in their 30s.   Now in my late 40s with 2 school aged kids, my wheelhouse for men seems to be divorced guys who had children  in their 40s and they are now in their 50s.

        So in my experience, the factors that most affect your dating life when you are a single parent are your age and life stage, the number of kids you have, and the kids’ ages.   Also one big thing I had going for me is that I had no ex/baby daddy drama.   I’m not intermittently or perpetually irritated and frazzled by coparenting and child support issues.

        As for what I would tell single moms or women who are contemplating being a single mom, first I would tell the single mom’s by choice that being the parent of a newborn or a newly adopted child is a status incompatible with dating.   Bond with your child by spending as much time with them as you can to give them as secure of a base as possible.   Adjust to your new life and figure out your routine and support system.   Then as you get more chunks of time for yourself, take care of yourself first.   Exercise, get your hair done, spend time with friends and family, and eat well.

        When a SMBC or a divorced mom feel grounded enough to start dating, it’s important to realize and accept that there will be men who will not want to date or be in a relationship with you because you have a child.   Don’t take it personally.   And never, ever spend time and energy trying to convince a man who had decided this for himself that he should change his mind and go out with you.   It won’t end well.   Likewise dump a man who is ambivalent or hostile to either your role as a mom or to your kids.

      2. 4.1.2

        I thought being a single mom that im pretty much doomed to be alone for the rest of my life. but ill admit that hasn’t been the case because guys still checking for me in terms of attraction and wanting to be with me. now I did wonder even quite recently if me being a single mom has anything to do with the reason Ive been taken for granted….but then again I do also know that being taken for granted is do to allowing myself to be taken for granted lol so I cant say yet for sure….

    2. 4.2

      I wish I could date more like the single childless women. that is definitely a major difference. but my responsibilities are my responsabilities and we just do the best we can and make some bomb lemonade out of our lemons.

    3. 4.3

      I think it depends how many kids one has and what age as well. When they her I have four I right away get uncontrolled exclamations: oh you almost have a basket ball team blah blah. Then they ask ages: oh you got Irish twins lmfao

  5. 5

    I am a single female foster parent dating a single dad.   I began dating him when I was getting my foster parent certification. His daughter is very close to her mother and did not really approve of his dad having a girlfriend.   I did   not have a great relationship with my boyfriend’s daughter but she totally adores my foster child and only really starting wanting to spend time with me once the foster child came into my home.

    As far as adoption, I did try to go that route and it is very difficult for a single woman.   Many birth mothers will choose the two parent family given the option.   Also the expense is daunting.   Easily over 20K and often closer to 40K.

    Being a foster parent is not the easiest route but I do think it is very worthwhile.

  6. 6

    As a single adoptive mom of teenagers I think if I had to do it again I would try LoveU for 6 months before adopting.   It’s only a 6 month delay.   When my kids were small and the date was a dud and I had to jump through lots of hoops to make the date I lost interest fast.   The price for a dud date went way up once I had kids.   It’s not just the job, it’s the commute and finding yet another sitter.

  7. 7

    I loved the second caller because Evan showed that we men are always trying to do two very important things on a date with women regardless of the circumstances.

    We try to:





    I think the problem arises when our method of doing these two things are misunderstood by women.

    Which means that we basically failed to bond or impress her.

    Whenever I hear a woman telling a story about a man who talked to much about himself on a date (impress) or of a man who didn’t talk enough about things that she felt were important and wanted to talk about (bond); I usually just think he is a clueless man. But women interpret it as him being selfish and therefore he is eliminated from her list.

    Dating really is a skill.

    1. 7.1

      lol not going to lie. I hate arrogance. and sometimes when a man comes off as arrogant I forget that maybe he is “showing his chest” so to speak to try to impress. so I try to remember this going forward now that I am back out on the dating scene and to be a little more forgiving the next time he is being this way.

  8. 8

    Evan you call it the politician answer but we millennials call it the Conway or being Conwayed.

    Named after Kellyanne Conway who is masterful at redirecting and dodging questions.

    Seriously, Vox interviewed a professional nationally awarded debater and teacher about Conway’s tactics.

    So maybe the single mom’s should study Conway on who to deal with men who use them as a therapist. Single moms should tell these men about the alternative facts

    1. 8.1

      I don’t know Adrian.   If a woman tried to “Conway” a man with evasion and alternate facts when he was asking reasonable questions, I’d say it would be perfectly understandable if he decided to interview someone else 😉

  9. 9

    I could really relate to the first caller’s feeling about fostering being something over which she had control, versus the dating process, which is contingent not just on our feelings, but a match with the feelings of another. The first feels far more obtainable. I think the trick is to find a way to feel like your needs (whatever they are) are met at a minimum level while also using your faith in the process to propel you to actions that are very likely to produce your ideal outcome.

  10. 10


    I was really impressed when you  dug deeper with Casey (caller #1) about the deeper issue of what her decision making algorithm was on her plans to be a foster to adopt parent.   Her call immediately reminded me of the recent letter you replied to on the blog about the woman who was two months pregnant but still wanted to date.   Especially in the situation of adopting, where there aren’t “accidents”, I just get an uneasy felling when someone plans to take on the huge commitment and responsibility of becoming a new parent, and then wants to know how to try and work dating into the equation as well.   It seems prudent, and simpler, to focus on one or the other, becoming a new parent vs. finding a life partner.   Casey, at 39, has time to spend a year or two making a full court press to find a boyfriend/husband.   If that doesn’t work out, becoming a foster mom won’t be any more difficult at 40 or 41.   And she will have greater peace of mind that she really tried to achieve her primary dream of a nuclear family before she moves on to a modified plan.

  11. 11

    I prefer your soap box style podcasts….we get more wisdom from you that sticks to the topic better than the time it takes to address specific questions that can easily dilute the topic itself. Like this should have been called should I be a foster parent/how early should I talk about my kids lol. So many things you could have said about single mom dating that would have been more helpful. I felt like that with your other podcasts of 2017 not just this one.

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