“Why Can’t I Get a Second Date?”


I’m 22 years old, and my first relationship ended a few months ago. Now, no matter what I do, whether meeting people in college or even trying dating sites for the past couple years, nothing ever seems to come out of it. Even when I go out with a guy who has the exact same interests I do, and we end up having a good time and having a lot to talk about, he always loses interest after the first date. Each of the guys has said I’m pretty, artsy, smart, and fun to be around, but none of them ever want to put in the effort when it comes to planning a second date. I honestly don’t know what I’m doing to turn these men off. Maybe it’s because I won’t sleep around? Maybe it’s because they just feel sorry for me and lie to me when saying that they really think all those things of me? If you can get back to me ASAP, that’d be great, because I don’t know who else to turn to. — Wanna Be Bride-to-Be

Here are five major things you’re doing “wrong”:

1. Even though, at 22, you’ve recently ended your first relationship, you say that “nothing has come” of any of the dates you’ve had in the last couple of years. Well, what would you call your relationship that ended a few months ago? Doesn’t that count as something? This, along with other signs, is an indication of a skewed perspective and unhealthy attitude. Rather than see what you’ve been gaining (experience, figuring out what you like and what you’re looking for in a boyfriend, fun/interesting dates, new friends), you’re focused on what you think you’re missing out on.

2. You’re waiting for the guy to plan a second date. Why don’t you put effort into planning it and asking the guy out? It’s 2016, lady; take the bull by the horns.

3. You’re giving the guys the power to do the choosing. They get to decide whether to have a second date. They get to decide whether you’re worthy to pursue (based upon, I guess, attributes like your being “pretty, artsy, smart, fun to be around”). What about who and what YOU want? Is there anything you’re looking for in a guy other than his being interested in you and putting effort into planning a second date? What about chemistry and a connection? You can think someone is good-looking and smart and artsy and fun to be around and not feel “it,” you know? Do you know what “it” is? Have you felt it before? If not, then that’s a pretty good reason why you haven’t had a lot of second dates, and maybe you should focus more on determining whether “it” exists between you and another person and if you even like the other person instead of whether he likes you.

4. You signed your letter “Wanna Be Bride-to-Be,” which is… weird. First, you’re 22. That’s awfully young to be concerned with getting married ASAP. Second, to be focused on being a bride suggests you care more about finding someone to fill a role (groom) than in finding someone who awakens something in you and fills you with love and optimism for the future. It suggests you’re more into the idea of a special day (a wedding) than of a relationship or creating a life with someone. It suggests you might have a princess fairy tale complex in which you only need to fill the prince role to live happily ever after. It suggests a disconnect (and a disinterest) in reality — of getting to know someone, like really know him — his flaws and his attributes and how they work with your flaws and attributes, and what his life goals are and what makes him unique and special and worth spending every day with for the rest of your life (which could be 80 years, so you better really know — and like! — what you’re getting).

5. You’re projecting your insecurities on guys you barely know. The whole “maybe they feel sorry for me so they lie to me about thinking I’m pretty” thing is the sign of self-esteem issues. Could it be that they really DO think you’re pretty but don’t plan a second date because: They don’t think you like them? Or, they didn’t feel a connection because there’s more to connecting with someone than simply finding her attractive? They got the strong impression from you that you were looking to fill a role rather than get to know them and that didn’t appeal to them? They got the strong impression you were looking to jump into a super-serious relationship with sights on a wedding ASAP and that didn’t appeal to them?

Bottom line: Slow down; shift your focus (from a wedding to getting to know these guys and enjoying your time with them, whether it’s just one date or a series of dates that may lead to a relationship); figure out what you’re looking for beyond a place-holder/role-filler in your fairy tale; build your confidence outside the validation of boys’ opinions of you (seek validation from friends and family and your accomplishments and the contributions you make to your community and society). You are young and have so much life ahead of you in which to find love and serious relationships and even the husband you think you’re ready for. It will be a happier occasion if you allow it to happen organically and with the right match rather than trying to force it with whoever likes you well enough.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. I think it only takes one date for these guys to identify you as a ‘wanna be a bride’. That has to be awfully scary coming from a woman they basically don’t know, have spent a couple of hours with, and haven’t slept with. When they ask you to tell them something about yourself, is your first response to tell them your ring size?

    1. Yes, I was thinking this too, as soon as I say that as the sign off, I was thinking, I need to find out if this is a Wendy created name or if the LW used this, so I’m glad Wendy answered that, because I have a feeling they way she feels might come through on her dates.

  2. I agree with everything Wendy said except for number 2-that you ask them out again. If it is left to the guy to do the asking ,then you know he is interested if he asks, and not just being polite. If he does not ask, do not contact him and move on. This may sound old fashioned but it makes sense to me.

    1. NO. Sometimes guys are just stupid, and lazy, and will let a good thing pass for no reason. I would say it can do no harm at all to be the one to reach out for the second date, and I think a lot of the shyer guys would enjoy this.

      1. honeybeenicki says:

        Yes! Some guys are also wondering the same thing as the LW – well, does she really like me? I don’t want to ask her out and get turned down, etc.

      2. In my opinion, the “harm” is that: (1) you’ll get a lot of “no’s” the way that guys get a lot of “no’s” when asking girls out, and if you’re not easily able to brush that off and breeze through it (what 22 year old girl is?) then you’ll just become way more insecure, or (2) pushing the issue will cause you to waste more time going on second and third dates with guys that weren’t into you enough to want a relationship, but were too nice to say no. And, who wants to find themselves dating a “stupid” or “lazy” guys anyway? I feel like if a “shy” guy is able to ask you on a first date, they’re going to have the courage to ask you on a second if they’re into it.

      3. Ah gotcha, girls are too feeble to get a no, but guys are perfectly fine to get them. Good to hear.

      4. SpaceySteph says:

        Eh, not girls in general, but about this particular LW.. well, T may have a point.

    2. Maybe she doesn’t need to ask him out, but she should definitely follow up. If I had a really good time on a date and was interested in seeing someone again, I’d follow up with at least a text telling that person I had a really good time. It lets that person know you’re interested in a second date. Maybe he or she wasn’t sure. That solidifies it. And if that person doesn’t respond, you know for sure not to waste brain space.

      I especially send the follow up text saying thank you if he paid or if the date ended awkwardly. Because. 1. Manners. and 2. I don’t want there to be confusion.

      FWIW, there has only been twice in my long dating career where I wasn’t asked on a second date. One was a set up from a friend. This guy took me on a date because he didn’t want our mutual friend to know he was dating this coworker. The other was from an OK cupid date and whatever.

      1. Seriously, are you Heidi Klum?! Lol. I have been on TONS of first dates that never turned into getting asked on a second, and I feel like I’m a pretty good package. On a first date you simply don’t have any type of commitment to each other yet, odds are you won’t click with most people, and it’s easy to not follow up. I say this to point out to the LW that what she’s experiencing is completely normal and just part of dating.

    3. Avatar photo muchachaenlaventana says:

      why does it always have to be the dude asking the lady out on the date? how are we ever going to have any sort of equality between sexes in any real way when idiotic norms and ideas about this just will not die. the more men get used to women being on equal footing, the less it should be “dude puts forth all of the initial interest and controls the entire dating process while the lady is a passive bystander” which gives men all of the power and takes away agency from females. I think hetero normative couples and people who are dating can probably take a lot of cues from people w/i the broader gender/sexuality dating spheres. If you are interested in a person after a date, regardless of which sex/gender you are, you are more than capable of asking them on a second date. If they say no, they aren’t interested. Case closed.

      1. Avatar photo mrmidtwenties says:

        Preach. While we’re talking about equality, I’m also curious if the LW has ever offered to pay on any of these first dates.

  3. One thing that struck me was that you ended your letter: “if you can get back to me ASAP…” That sounds like someone with a timeline, not someone who is interested in finding out the answer to a question. That’s how you write to someone you’re working on a time-sensitive project with, not someone you are hoping to go on a date with, IMO. Are you naturally impatient? That could be part of the problem. When you contact these guys, do you tell them to get back to you ASAP? It just kind of stood out to me. I would be reluctant to go on a date with someone who put pressure on me to respond immediately.

    1. Yes, it ore than kind of reeks of desperation.

  4. for_cutie says:

    I have a hunch about what is going on here: you’re 22, just graduated college, right? You probably have college friends getting engaged, planning to marry their college sweethearts, and you’re not, am I right? Maybe you’re even in one of those sororities that is all partnered off and you’re the single one, maybe? I remember a year or two of weddings post college graduation. Some marriages lasted, some didn’t. It was my first exposure to weddings really, and there were quite few in my social circle.

    You’re 22. You should be focused on you, your next step in life, career, grad school, whatever. When you throw yourself into bettering yourself, you will meet like-minded people. Some will be great friends. Some may end up being more. Dating should be a fun distraction from working on your personal goals. You sound like dating is your “job” with a goal of Mrs. This is not the 1950’s so men can probably pick up on this and probably want more for themselves than bagging a wife.

  5. There is a joke told by the foreign policy crowd that diplomacy is the art of learning to calmly and soothingly repeat ‘good doggie, good doggie’ as long as it takes to find a suitably-sized rock.

    I think this explains all the wonderful things guys say about you on first dates. They just want to make it through the experience without either of you getting hurt in the process. To them, they were taking you out on a brief, low-pressure, get-to-see-if-there-is-any-interest exploratory first date, while they saw you as starting the stopwatch on ‘six months until the ring’.

  6. Katmich15 says:

    “Each guys has said I’m pretty, artsy, smart, fun to be around” Maybe it’s just me but I found this a little strange, why are they telling you that you’re artsy and fun to be around? Those don’t seem like first date comments, it almost sounds as if they are trying to reassure you. I can see them telling you that you’re pretty or smart, things like that, but the others don’t sound like things that someone would just say to you on a first date. Again, maybe it’s just me, but I wonder if you are projecting insecurity to them. Think of dates as their audition for you, not in a snobby way, but a chance for you to decide if they are someone you enjoy being with and if “it” (to quote Wendy) is there.

    1. These definitely sound like first date comments. I’ve been on MANY first dates in the last two years and guys say this shit ALL THE TIME. “Wow, you’re so pretty, you’re so much fun, this is great, I’m having such a good time, you’re so articulate, I really like you, etc, etc.” I think a lot of guys say these things because that’s how they feel in the moment. They are having a good time, see something they like about a girl and compliment her, and it’s the truth.

      But that doesn’t necessarily mean they see a future with that girl, it doesn’t mean they want to keep dating her, it doesn’t mean he’s going to wake up the next morning dying to see her. Especially young guys. They haven’t figured out yet that saying these things make a girl think they want a future with her.

  7. LW, I know at 22 it feels like you’re a grownup and ready for a serious relationship and ready to start your new adult life. You watch your friends get engaged after college and you think you’re getting old and falling behind. I don’t say this to sound condescending, I had the same feelings at 22, but looking back I still had so much to learn about myself and relationships before I could be good at them or choose the right person. I am SO glad I didn’t end up with the person I was dating when I was 22 (or for that matter, any of the guys I thought were just dreamy at that age). And LW, guys take longer to mature and be ready for a serious relationship, so a huge part of your problem is that most of your peers do not want to jump into a relationship, they want to go on casual dates with multiple people. I’m impressed that at 22 you’re even getting a bunch of first actual dates and not just casual “hangouts” that aren’t really dates. Also, even at any age, my experience is that most dates with people you met online never progress to a second date – odds are you won’t click that much with a stranger, and people just don’t take a first date that seriously.

    That said, my guess is that where you’re going “wrong” is that you want this so badly, that you have an air of impatience and desperation. Guys can smell that the way dogs can smell fear. (For this reason, I think the advice that you should take initiative in asking for a second date is way off-base, and will just make you feel worse about yourself when you get a “no”.) Some things you might be doing wrong:
    – pushing the issue of a guy taking you on a date (e.g. by constantly “running into him” or mentioning that you should hang out), when really he wasn’t that into it to begin with, so it was never going to go past date one
    – asking the guys what they think of you while on the first date, or fishing for compliments
    – talking about your previous relationship or why you are now looking for another serious relationship (you don’t want them to think you’re just looking for a replacement for your ex)
    – texting them right away after the date before waiting to hear from them

    But really I think you just need to be more patient in waiting for the right person to come along. Don’t settle too early, and don’t date much older guys just because they’re the only ones that will take you on multiple dates – you’ll end up wasting more of your time when down the line you realize you picked the wrong person.

  8. Avatar photo mrmidtwenties says:

    There’s another option, the LW could be just a shitty date. That’s not saying she’s a shitty person, but a person can be great on paper, great as a person, but be a terrible date. There’s been plenty of people I’ve been out with who I’m sure are great people, we seemed to have chemistry and lots of things in common, but were not good dates. One pretty common theme among those dates was reeking of desperation, which this LW seems to be.

  9. Another Jen says:

    Wanna Be Bride-to-Be…yikes! That’s probably a big part of the problem right there. “I want to be a bride” and “I want to be engaged” are a lot different than “I want to share my life and possibly have a family with someone I love deeply.” Being a bride lasts for 1 day…it’s a wonderful experience for many, but it might help to see it as 1 important milestone among many, rather than a goal in-and-of itself.

    Maybe shifting your focus to “I want to be happy” or “I want to have deep, loving friendships with people who share my interests and values” would be a good start. 1) It’s a great way to meet people who know people, who may be 2nd-date-worthy. 2) You’ll be building a life that’s worth sharing when “the one” comes along.


  10. Many men can sense desperation.

  11. If part of the issue here is that a lot of your friends are getting married right now, let me say that there is a good upside to being one of the last of your friends to get married. You get to see how it’s all done, figure out what’s good and what’s just a stupid waste of money (ahem, favors). I didn’t even really have to interview vendors or anything, I chose people that did a good job at my friend’s weddings. I feel like so many of my friends that got married young have things that they regret about their wedding, cuz they just didn’t know any better. So LW, live your 20s, have fun, and if you meet an amazing guy that might someday be your husband, awesome.

  12. bittergaymark says:

    Everybody beat me to it… but damn. This letter SCREAMS I am DESPERATE!

  13. SpaceySteph says:

    I think a lot of commenters hit it on the head that the LW is graduating and some of her friends are in long term relationships heading toward young marriage and she is feeling like she needs to settle down quick.

    I didn’t start dating my husband until I was 24 though and he’s way better than the guy I was dating at 22. Just live your life and don’t compare it to your friends. Just think, if you don’t get married until you’re 30, it saves you from being a divorcee in your 20s!

  14. artsygirl says:

    LW – It sounds like you are putting too much pressure on your self and your dates. Dating can be hard, especially after the end of a long term relationship, you analyze every minute detail in the hope of figuring out if it went well or poorly. The fact that you have not been asked out for a second date must be hard on your self-esteem. But as Wendy said, did you actually want second dates with every guy you have met? I think it might actually be smart for you to walk away from the dating scene for a little bit. Maybe pursue some fun hobbies, take up a class, do something that YOU want and makes you better so you are not agonizing over if you have a boyfriend/fiance or not.

  15. MissAnneThrope says:

    LW- you need to spend some time, like most other commenters suggested, and figure out what it is you REALLY want. IF you still really want to get married, what type of guys are you going out on dates with? If you’re going out with college graduates who are around your age, the fact is most of them are NOT looking to get married any time soon. I read the article I’m linking below that I read a few weeks ago. While its not “advice” I think its interesting because its someone coming at an “age old question” from a difference perspective.


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