“Should I Tell The New Woman I Have a Pre-Scheduled Formal Date?”

I went out on a “first” date last night with a former girlfriend, “Rhonda,” whom I dated five years ago and who contacted me out of the blue two days ago. We hit it off again like nothing had changed, and I want to possibly see where it goes with her this time. The problem is I have a very important formal event out of town in two weeks that I asked a friend, “Kelly,” to go to with me (platonically) because I wasn’t involved with anyone when I had to make reservations/airline tickets for the event. Should I tell Rhonda about it or how should I handle it? — Pursuing a Former Flame

Of course, you’re doing nothing wrong and don’t really owe Rhonda an explanation, but because you have a personal history and you’re interested in potentially reigniting the flame, I would err on the side of transparency. The next time you talk with her, be honest — after telling her you had a great time on your date and would like to go out again, tell her that you’ll be going out of town in a couple of weeks and attending a formal event with your friend Kelly, who agreed to be your date since you weren’t romantically involved with anyone when you were invited to said event.

If a relationship with Rhonda progresses over the next couple weeks — if there are dates and communication between now and the event — I would make sure to keep in touch with her while you’re away to let her know she’s on your mind. A few texts — maybe a picture or two of you dressed in your formal wear — and some commentary on the event can go a long way. If she gives you any grief though, I’d take that as a red flag and extinguish those kindling flames pronto.

I have been in an online, long-distance relationship with an older man for several years. We have never met. I have recently met someone in real life whom I feel a great deal for, and my feelings for my online LDR have dwindled. I have tried to end my LDR before, but he threatened to kill himself and I felt I couldn’t leave him. I know this will hurt him and I hate that, but I don’t know what to do. Any help please? — Need Help Disconnecting

Your online friend is manipulating you and you need to take your life back. Do NOT let him make you feel guilty about ending a relationship that does not satisfy you. Even if his threats are not empty ones — and I think they are — you are not in charge of his happiness. You are not responsible for his well-being. You deserve to have your freedom to pursue something real, with someone you can actually see face-to-face and touch and get to know in person.

Tell the online guy: “This relationship is no longer working for me and I am moving on. I wish you well, but please respect my decision and no longer contact me.” You don’t need to tell him about the new person you’ve recently met, but you do need to be firm about your decision and the boundaries you require and deserve. If he does not respect your boundaries, block every way he has to contact you and DO NOT respond to him, do not engage.

I hope it doesn’t come to this, but if he threatens you in any way, you should continue not to respond to him and should contact the police. Someone who threatens suicide if you break up with him is not stable, and you need to protect yourself and your privacy accordingly.


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


  1. wobster109 says:

    LW1 – A heuristic I use is if I feel awkward about saying something, then I say it just to be sure. For example, I’m friends with my ex, and we had ramen after rock climbing, and it was just my ex and me that day. The climbing group is 5 people total, and 2 people out of 5 showing up is pretty common. I was tempted to make it sound like a group thing, so once I recognized the squirelly feeling, then I really had to be honest. But even if the individual conversations are awkward, being transparent builds trust in the big picture. By the way my bf wasn’t bothered by it. He trusts that I wouldn’t hide anything.

  2. LW1: I would wait still a bit to see where it goes with your former girlfriend before speaking to her of this event. If you have no romantic interest in Kelly, but she is simply a friend, then it is easy to say so soon before the event, and to make no big deal of this information. There is no reason for Rhonda to be jealous, right?
    It is clear that the beginning of a relationship – if it does go this way, which you don’t know yet – is transitional. Don’t let yourself feel guilty of anything here, just say that Kelly is just a friend.

  3. I think the fact that he mentions “formal” affair with Kelly says that it is a little more than just friends, even if he does not see it yet.

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